


Symbiosis

by azo_dye



Category: Supernatural
Genre: Big-Ass Paintings of Eyes, Blow Jobs, Castiel has skewed ideas of sex work, Chicago, Denial of Feelings, Dom/sub Play, Domestic Fluff, Frottage, Idiots in Love, M/M, Non-Penetrative Sex Toys, Painter Castiel, Porn with Feelings, Pretentious Color Names, Sex Toys, Sex Worker Castiel, Sugar Daddy
Language: English
Status: Completed
Published: 2017-07-17
Updated: 2018-09-06
Packaged: 2018-12-03 06:51:26
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 22
Words: 96,180
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11526846
Author URL: https://archiveofourown.org/users/azo_dye/pseuds/azo_dye
Summary: Castiel has a million problems: rent, getting enough hours at work, tuition, his nonexistent personal life, and the fear of losing his voice from deepthroating too often... but a starving artist has to do what he must.What Castiel really needs is a permanent arrangement, just until he can get a grip on his down spiral of a life.





	1. Prelude to a Deal

**Author's Note:**

> Hello everyone! Anyone want to take a guess at how long this was in my folder? 
> 
> Welcome to Symbiosis, the story that explores love, loss, vibrators, and some art history as well. All mentions of sex work and Sugar Daddy/Baby relationships come from my own experiences and studies. Any character resemblance to anyone is unintended and thoroughly accidental. Will add tags as they become relevant. 
> 
> Enjoy!
> 
> -azo

Castiel spat neatly onto the ground beside where he kneeled, wiped off his chin, and stood up. “Twenty bucks is what we said, right?” 

The bald man shakily did up his fly and fumbled for his wallet out of his back pocket. Castiel didn’t say anything as the man fished out the bill and held it out to him. Castiel grabbed the bill without actually touching the man’s hand. He turned to go without saying any more, drawing his collar closer to his neck. It wasn’t cold, but he couldn’t shake the unpleasant chill that kept running down his spine as he walked away. 

He made it almost halfway down the block.

“Wanna make it fifty?” The man called behind him before he got to the cross street. 

Castiel looked around with his ‘customer’ smirk firmly in place. “You’re ready to go again that fast?” 

The man chuckled, but it just sounded tired. “Nah, but I could be in an hour or so? You wanna go back to my place? Maybe have a drink?”

Castiel fought a shudder and waved a hand. “Maybe some other time. I’ve got places to be.” He turned again and hustled as fast as he could without running to the street corner. 

Castiel snuck a glance at a man standing on the street corner caddy corner to his, blanketed in shadows. This man was heavyset with a bald spot noticeable from across the street. He was currently making lewd gestures at Castiel. 

Sighing, Castiel drew his arms into his sides, shuffling in the opposite direction of the man. Just because he sucked dick for rent money didn’t mean he couldn’t be selective when he wanted to be.

The streets in this area were a disgrace. The city government liked to tell visitors that they cared “aggressively” about the appearance of their city, but Castiel didn’t see how they possible could with the sheer size. Castiel skirted a strange smelling puddle and kicked a loose cigarette butt out in front of him, crushing it with his ratty trainer as he walked on. 

Castiel felt his stomach rumble and he put his hand to it. He had twenty bucks in his pocket, technically, he wasn’t as broke as he was an hour ago. He could stop at the McDonald’s he knew was at the next intersection if he really wanted to. He considered it briefly before shaking his head. He had eaten that morning and he had more pressing debts in his future than what a cheeseburger could rectify. 

He needed money, there was no way around it. Between rent and his upcoming semester, to say things were getting tight was a bit of the biggest understatement of the century. His job at the bookstore only covered so much, and Chicago wasn’t the cheapest place to live. However, there also wasn’t anywhere else Castiel could see himself living. Not with the program offered at the Institute and the doors it could open after graduation.

If he made it to graduation.

Castiel glanced around the empty park briefly, before taking a seat on the bench. A wad of gum was stuck unattractively to the seat next to him. He pulled out his phone and tapped through to his Arrangement Seekers app. A little flag told Castiel he had five new messages, two of which were requests to see photos without even a conversation starter. 

Castiel ignored those. 

He scrolled down to a new message from menage-a-douze35. Castiel supposed there was a joke or clever double entendre here, but he didn’t speak French. The man’s profile picture wasn’t much of a picture at all, just a closeup of what Castiel assumed was an impressive engine block. Castiel hadn't seen the inside of a car that wasn’t rusted within an inch of its life and its owner’s wallet in a very long time. 

menage-a-douze35 says:

_Hello! Just dropping a line to see if you'd be interested in meeting any time soon! I’m in Chicago for a week on business and I’m looking for some fun! You will be heavily rewarded for your time… provided we have a connection of course! Lets trade numbers if you’re—_

Suddenly, a text popped up from a number replaced by skull emojis. 

>> Incoming:  
_I see you…_

Castiel whipped his head around wildly. The bushes to the right of his bench rustled for a second before a pale girl with long red hair stepped out, a huge grin on her face. 

“ _Anna._ ” Castiel glared. Anna cackled and sat close to Castiel, avoiding the wad of gum when Castiel pointed it out to her. Castiel brandished his phone at her. “Change it back. I don’t wanna freak out again if I’m with a client and I get a text from Three-Skull Rando.” Anna rolled her eyes but took the phone. 

“Who else would change their contact info? You have like, what? Three contacts? Isn’t this your burner phone anyway?” Anna’s mouth was ticked up in a way that let Castiel know she was teasing… mostly. “How’s business tonight?” 

Castiel shrugged. “Not bad. I got twenty off the last guy, and I was going to head down to that new bar on the West Side to either pick up a shift or get picked up.” 

“Rent’s due in a few days.” 

“Stellar. Better put in double time on that arrangement app while I still got my good years in me.” 

Anna slumped down next to him and tossed Castiel’s phone back to him. “How does that even work? You scroll through a list of people to call Daddy and just pick one?” 

Castiel held his phone between them as he opened the app to the message from menage-a-douze35 again. Anna wrinkled her nose, but giggled. “Come on, click on his profile, he’s gotta have a mirror selfie or two. Oooh Castiel, maybe he’ll have a gym pic! Wouldn’t that just be dreeeaaaaaammy—?”

Castiel grinned. “Anna, if you’re going to be difficult, I won’t let you help.” 

“I can’t really say this is helping you or me. Look at him, he’s balding.” 

“… you’d never make it as a sex worker.” Anna shoved him playfully. They laughed at the johns’ obvious ego problems, combined with their sometimes desperate come-ons. Anna helped Castiel make plans with menage-a-douze35 to meet at a bar on the South Side later that night.

After a while, Castiel put his phone down and just sat in silence with Anna for a moment. This was his favorite part of their friendship. They never judged each other for doing what they had to, and having that kind of unconditional support was better than any tipping customer. 

Castiel yawned. “So where have you been all evening? You weren’t home when I left.” Castiel and Anna shared a dingy studio apartment. Usually the two were able to keep constant tabs on each other, for safety reasons, but their schedules sometimes lured them out from the other’s watch. 

“I got called in because Becky sprained her ankle… again.” 

Castiel raised his eyebrow. “Do we… not believe her?” 

“Nah, that bitch is pregnant. I just know it.” Anna said it with such a straight face and with such solemnity, Castiel found himself chuckling. Becky-From-Work was Castiel’s favorite of Anna’s gripes. The burlesque club where she worked had a group of seven incredibly talented dancers, but none of them seemed to be able to get along for more than two weeks. Someone was always getting on another’s nerves or stealing her tips. Better than a soap opera for those who didn’t have cable. 

Castiel shrugged and pulled out a pen, searching his pants and jacket pockets for some paper. When he came up empty, he turned to Anna, who was already offering her smooth, pale forearm. Castiel uncapped the pen with his teeth and spoke around the plastic. “Gotta love the extra tips though, right?” Dark lines of ink started to flow across Anna’s skin, feathering in places, and taking structure in others. 

Anna huffed a sigh. “I guess. Just feels like we’re all getting ‘called in’ all the time. If we’re that short-staffed, why doesn’t Keith just hire more dancers?” 

“Not everyone can dance as well as you, Anna. Some of us have to resort to our more basic human instincts to put bread on the table,” Castiel said, cap still between his teeth, smirking all the same. 

“I have a gluten allergy, and our table is two milk crates.” 

Castiel finished his sketch and recapped the pen, admiring his work, allowing Anna her arm back. “Well, it doesn’t change the fact that you’re a stripper, and I suck dick for money, and together we’re just trying to get through art school. Alright, go ahead, guess the artist.” 

Anna stuck her tongue out at him as she studied his work on her arm. “I’m a _burlesque_ dancer.” She squinted at the ink on her arm. "Um... you already did Monet, and the face looks too normal to be Picasso... he's the one who paints the weirdo alien faces, right?"

He rolled his eyes. "It's called multi-perspective, you absolute Philistine." 

Anna, best friend that she was, answered with a comically low-pitched mockery of his voice, with her face scrunched up like she'd just smelled something unpleasant. 

Castiel playfully punched her arm. “Whatever, come on. I gotta hot date tonight.” He tried to keep a straight face, even though Anna was gagging between fits of giggling. The two stood and walked arm-in-arm to the end of the block. “Are you going in again later?” 

Anna nodded. “Might as well. I’m on break now, so I’m supposed to be like, resting or something. But if I don't go back to work the evening crowd, it’s like giving up money on purpose.” 

“You should do that one number with the hula hoops.” 

“That’s literally the worst number Stella ever choreographed. I don’t know why you think it’s funny.” 

“Oh come on! It’s cute! With the—“ Castiel mimes swinging a hula hoop around his narrow waist, “Classic crowd pleaser. And with the tassels?” Anna shoves a laughing Castiel into the bushes, but helps him up after. In all truth, Anna could make any routine seem effortless and beautiful, she was a wonderful dancer. 

“Did I tell you what Professor Harrow said last week about my pointe routine? He said he wants me to teach it to the intermediate class!” Anna was at the Art Institute of Chicago for their dance program. According to Anna it was the stuff of legends, but Castiel spent his time in the painting lab, he rarely saw anything that constituted as legendary. 

Still, he was happy that Anna’s talent was being recognized. “That’s great! See, I told you you should be teaching, instead of up on a pole.” Anna thwacked him again in the chest, but it was much more halfhearted this time. She knew it was true. 

They walked until they reached their usual train station. Anna dug her pass out of her wallet and gave Castiel a quick hug. “Don’t be out too late? And if I’m not home before you, can you go ahead and start the dishwasher?” 

Castiel nodded. “Wait, you never guessed.” 

Anna held up her arm. A collection of delicate lines crawled up her arm in painterly strokes, unclear as individuals, but a vivid image of a ballerina together. “Hmm. Degas?” 

“Very good! I mean, I was taking it easy on you, but—“ The sound of a slap echoed throughout the empty street, followed by the sounds of their shared laughter. 

…

Castiel generally tried to keep all thoughts of his mother away while he was “on the job”, so to speak. He didn’t like to think of what she would think of her only son, a farm kid from Illinois, taking money from strangers to pay rent in exchange for a half hour of his time and an orgasm. He wondered if she would call him a whore. He’d been called that plenty of times, mostly when the guy wanted to take him home and he refused.

Even so, Castiel couldn’t help but feel a tiny bit sleazier than usual sitting at the bar of a dive that even he knew to stay away from. He tried to scan the bar without looking too obvious, searching. He pulled his phone out and tapped to the conversation between himself and menage-a-douze35.

>>Incoming:  
_im almost there. ill be in a red shirt and khakis so u can find me easy_

<<Sent:  
_What should I call you when you get here?_

>>Incoming:  
_my name is balthazar but you can call me daddy ;)_

Castiel pulled a face and put the phone away. Balthazar was fifteen minutes late. Color Castiel impressed. If rent wasn't due next week, he would have walked out, no questions asked. One of the biggest perks of tricking on the side was being able to set the worth of your product—your time. If someone wasn’t meeting your standards, you were free to leave. Media made the job seem luxurious, like men were waiting to lavish expensive gifts and trips on the people they paid for their time, just their time. The truth of the matter was that even people in a sugar daddy arrangement had to sacrifice a lot to earn the big gifts they wanted. It was never easy, and rarely glamorous, but that’s what separated the amateurs from the professionals. 

True, Castiel had never gone much farther with a john past sucking their dick, but hey—he had only really been in the game for a few months now. He was prepared for what he had to do. Or at least… he thought so.

So he’d call the SD “Daddy” if that’s what they wanted, present himself in the best light possible, like spending time with him was a delight that had to be earned. But he was also never one to turn down a twenty for some time spent on his knees. There was a line in a movie somewhere, “If you’re good at something, never do it for free.” 

Castiel took a sip of his water glass, no alcohol on the job, thanks. Plus, he had to go to his real job in the morning. The bookstore on the other side of the Institute’s campus had a musty sort of feel to it, with an even mustier owner, who did not appreciate any sort of impairment on the job. 

The clock moved another few ticks with no sign of Balthazar. This bar really was on the lower side of his usual haunts. It was dressed up like an old motorcycle bar, and located in one of the danker neighborhoods of the South Side. Castiel counted only three men in the entire establishment that didn’t have a full beard or mustache or both. There was also the lingering haze of beer breath and smoke that didn’t smell like it was from a cigarette. Why Balthazar suggested this bar, Castiel didn’t know. 

A man in a leather jacket bounced an eyebrow at Castiel while he was scanning the bar again. Castiel blinked at him, unsure of what such an attractive stranger was doing in a place like this, but looked away after a moment. He was supposed to be focused solely on Balthazar right now, it wouldn’t look good if another man came wandering over inquiring after Castiel’s interested gaze. Castiel resolutely looked towards the door. A man in a red shirt walked in. Castiel made to stand up and make himself seen, but the man immediately embraced a petite brunette near the pool table, forcing Castiel to take his seat once more. 

This was humiliating. Everyone probably knew that he was waiting on a blind date, one that was clearly very late. He glanced over at the stranger in the leather jacket again. He was supposed to be here for Balthazar… but Balthazar wasn’t here yet. 

The stranger was still looking at him, a tinge of amusement coloring his handsome features now that he had Castiel’s attention again. He didn’t seem to be with anyone, just sitting at a table by himself, enjoying the noise and atmosphere of the bar. He seemed to fit without fitting in at all. He had the biker boots and jacket of anyone else here, but he looked different. Softer, somehow. Like this was a costume he was wearing for the day, while looking completely at home where he sat. 

He was currently eyeing Castiel up and down like he was a dessert tray. His tongue peeked out, a shade of pink Castiel could see over here, and wet his full bottom lip and disappeared again. Castiel cleared his throat and pulled his attention back to his phone, as it buzzed.

>>Incoming:  
_hey angel can we reschedule? got caught up wit something. sorry :(_

Castiel snorted. Typical. He downed the rest of his water, and hopped off the stool, turning to face the rest of the bar. He took a step towards the exit, and stopped. 

A quick glance to his right told him that the stranger was still looking at him. He was also still very much alone. Castiel chewed his lip for a second. Might as well try to salvage the night. Plus, it wouldn't be too much of a hardship to have this stranger’s cock in his mouth. He might even do it for free. 

Maybe. 

Castiel rolled his shoulders back and turned towards the handsome stranger. He felt a genuine smile, not just his customer one, bloom across his face to meet the man’s widening grin as Castiel came towards him. 

“Hey,” The stranger greeted him, flashing a row of perfectly straight white teeth. “Break my heart and tell me your date’s waiting for you out in the car.” There was a challenge in his eyes, but it was playful. 

“No, change of plans. I’ve got a free evening.” Castiel stared him down, calling his bluff. He indicated one of the chairs. “Is your date coming back?” 

“Just arrived actually. Real looker of a guy, messy dark hair, big blue eyes, you’re a dead ringer for him.” The man gestured for him to sit down. 

Up close, it was worse than Castiel could have ever imagined. The man lifted his glass to his lips, giving Castiel a once-over again. 

Castiel knew he was staring. The man’s eyes were green. And not just green, but green. The kind of color you see in pictures and wonder if it was photoshopped. The color you forget eyes can be. The kind of green that makes you think of leaves, lit up by the sunlight and made to glow. 

“Do you want me to suck your dick?” 

The green-eyed man coughed, but looked up from his drink with a smirk on his face. “You tryin’ to seduce me, kid?” Like it was a joke. 

“Ye-es?” Castiel stretched out the word, trying to sound like the concept was never in question, but mostly just sounded unsure. It was rare that he was the one to do the actual propositioning aspect of his escapades. Usually, the other man would know exactly what he wanted and asked for it. 

“Pretty young to be in a place like this propositioning older guys, aren’t you?”

Castiel bristled and crossed his arms. “I’m old enough. Besides, the way you were looking at me earlier says that you still want me, no matter how old I am.”

“What are you, like maybe a day over seventeen? You’re attractive, no doubt about it. Didn’t know you were that young until I saw you up close, though.” The man said, scoffing. He really was very attractive, the low light smoothing out the hard planes of his face.

“I’m twenty-one, you ass.” Castiel said, before he could stop himself. This was rule one; treat the customer with respect. Shit. 

The man laughed and put up his hands. “Okay okay. I’ll give you one thing, your voice certainly doesn’t sound like you’re sixteen and three-quarters.” His eyes twinkled like he knew he was getting under Castiel’s skin and enjoyed the process. 

Castiel huffed, cheeks flushing a deep red. “If you’re not interested, I’ll just leave.” He made to stand up. So much for this plan. If he left now, he could make a train on the Red Line up to Roosevelt. 

The man’s voice stopped him. “And who are you going to go for next, hmm? Maybe that guy over there that looks like he eats little things like you for breakfast?” He glanced over across the bar by the window where a man easily three times Castiel’s weight sat, surveying the bar with beady black eyes. “I’m sure he’s real willing to take care of you.” 

Castiel glanced back to the green-eyed man. “I don’t have to stay here.” He said stubbornly.

“Oh sure, by all means, go out into the great wilderness of Chicago at night, looking for a john.” The man beckoned him closer again and he went. “You know that sounds like a Dateline case waiting to happen, right? Like, you know that; this isn’t news to you, right?” Castiel’s face hardened. He backed away from the table and made a beeline for the door, ignoring the green-eyed man’s protests behind him. He made it as far as the street corner before the man caught up to him. 

“Alright, wait, kid. Look, what’s your name?” 

Castiel paused. He never told johns his real name. He always went by his middle name, James, as it was fairly common. 

_“Hey, Joe, you ever hear of a twinky sex worker named James?”_

__

__

_“Sure, Tim, there’s ten of them working down at the Hotel.”_

Castiel balled his fists. He wasn’t entirely sure he could get out of a confrontation alive, if this even was a confrontation, but he figured he could do enough damage to make him back off, or at the very least, make enough noise to call attention to the situation if he needed to. He turned to face the man. “I’m not going to tell you if you’re just going to harass me.”

The man held up his hands again. “I won’t, I promise. I just want to make sure you’re gonna be okay. I respect anyone that’s willing to make their own living, but Jesus, you should be safe about it.” 

Castiel glared at him warily. “This is my job, you know. I don't appreciate you lording over me like you're so superior. We weren't all born with silver spoons stuck in our--” 

The man sighed and stuck his hands in his pockets, cutting him off suddenly. “Look, can I get you something to eat at least?” 

Food did sound good. He hadn’t eaten all day and he wasn’t looking forward to a whole night of being hungry. “No funny business?”

The man smirked. “Not unless you want it. But you gotta tell me your name first.”

Castiel crossed his arms and stared the man down for a moment. “James,” he said. 

The man rolled his eyes indulgently. “Not even a real name? What a pity,” he held his hands up in defeat. “Fine, James, I solemnly swear that I won’t touch you… without permission…” he adds with a wink. Castiel frowns harder. “Come on, hot stuff.” The man tucks his hands in the pockets of his leather jacket and takes off down the sidewalk, whistling as he goes, and expecting Castiel to follow. 

Castiel rolled his eyes and stood resolutely with his arms crossed for a moment, just out of spite. When the man turned back with an eyebrow raised, though, he huffed and started forward. He followed the man a few blocks south to a brightly-lit diner Castiel had never seen before. The place was relatively occupied, even given the late hour. A few patrons were at the counter sipping at coffee and picking over pieces of pie. An elderly couple sat in a booth in the corner sharing a plate of french fries. Castiel figured he would be safe here with people to act as witnesses in case the green-eyed man decided to kill him. 

A waitress with a blindingly pink uniform wandered over and unleashed her megawatt smile on the both of them. Castiel was sure he had only ever seen that particular shade of pink in medicine bottles.

“What can I get you boys? Our special tonight is pecan pie with ice cream.”

The man grinned easily. “Sounds good for me, and then whatever my friend wants.” He gestured towards Castiel.

Castiel scrambled for the menu, “Uh, just a cheeseburger is fine," he flipped through, picking the first thing he saw. "Yeah, that’s fine. Thanks.” 

The waitress left, leaving the two men in the booth in silence. Castiel fidgeted in his seat and tried to keep his gaze away from the man across the table, surveying him quietly. The man managed to leer without making Castiel feel unsettled or under a microscope. 

“My name isn’t James.” Castiel blurted out. 

“I know it’s not.” 

“I’m not going to tell you my real name.” 

The man smiled, not unkindly. “Figured not. I’d think you were kind of stupid if you had. Name’s Dean Winchester," the man smiled widely and Castiel had to catch his breath. "I’m the CEO of Winchester Holdings, LLC.”

“Is that your real name?” 

The man chuckled. “You’re smart. Yes, you can google me if you like, but I am telling the truth.” 

“Nice to meet you, Mr. Winchester.” Rule number two, refer to the john as Sir or Mister, until directed otherwise. 

He didn't say anything, but his eyes got a bit of a twinkle in them. The waitress brought their food and left her hand on Mr. Winchester's shoulder while she asked if there was anything else they needed. Castiel replied rather curtly, couldn't she see they were talking? When she left, Mr. Winchester watched her walk away for a moment with a tilted head before turning back to his companion. "Now, Not-James, you wanna tell me why you’re trolling for suckers out here in the middle of the night? Don’t you have school or something?”

Castiel flipped the top bun back off his burger and reached for the ketchup. “You wanna tell me what a CEO was doing in a garbage heap like that bar?” Castiel fired back. 

Mr. Winchester raised an eyebrow and smirked. “I know the guy who runs it. Or at least, I know him enough." He dug into his pie with audible relish. "So… why aren’t you at home in bed on a school night?” Pie crumbs fell out of his mouth. 

“I’m twenty-one.” Castiel said, curtly.

“Right, I’m sure your fake ID looks real convincing,” Mr. Winchester said, seemingly delighted at Castiel’s attitude. “But back to the school thing… you looking for a sugar daddy or something? Tryin’ to pay tuition?”

Castiel planted his elbows on the table and rubbed the bridge of his nose tiredly. “Mr. Winchester—“

The man held up a hand, placatingly. “Okay, sorry, poor word choice. Lemme try that again. So, young Not-James, you intend to finance your academic pursuits by selling your nubile body on the scary streets of Chicago?”

“Oh my god. I don’t fuck the guys I meet. I just blow them.” Just as Castiel said this, the waitress came over to refill Mr. Winchester’s water glass, and flirt with him presumably. She almost knocked the glass over when she placed it back on the table and scurried away without a word. She had definitely heard them. 

Mr. Winchester continued eating his pie, completely unfazed, if not a bit amused at Castiel’s outburst. His eyes twinkled as he smirked around his fork. Castiel lowered his voice. “I’ve hit a… a snag at home, financially speaking, and I either have to take on three more minimum wage jobs to pay for both a place to live and school, or I go back to working on my uncle’s farm for the rest of my life.” 

“You’re a farm kid, huh? Straight off the plains?”

Castiel rolled his eyes, “I don’t want to talk about it. I can’t believe I’m telling you all this. If you aren’t interested, can I just go? What do you want with me?”

“Just havin’ a conversation, is all. So come on, spill the sob story. You’re getting a cheeseburger out of the deal.” Mr. Winchester said, leaning over to steal a fry off Castiel’s plate

Castiel hesitated, picking up his burger and setting it back down twice before wiping his hands on his pants. “I hate Pontiac.” 

Mr. Winchester shrugged. “I’ve only been there a few times myself. Lotta air out there.” 

“It gets… draining.” 

“And you want out.” Mr. Winchester said it like it was a fact, not a question.

“Yes. I can’t do that anymore.” 

“And what do you want to do?” 

Castiel hesitated. “I want to paint.”

“You don’t have to go to school to paint, do you? Just gotta pick up a paint brush.”

“Right, but you also can’t get a job unless you have that piece of paper telling everyone you’re certified to do something you already know how to do. I have my program, I have a place there and everything. And I even have a few scholarships. I just… don’t have a way to pay for the rest of it.”

Mr. Winchester nodded, swirling another stolen french fry in the melted ice cream still on his plate. “What do you paint?”

Castiel shrugged. “Everything.”

“Everything?”

“I hate landscapes but big huge abstract pieces and lots of color and lines, that’s what I paint. Eyes too.” 

“You paint eyes?”

“Sure. Look.”

Castiel pulled out his phone and flips through a number of pictures of the things he paints and they’re huge floor to ceiling paintings of eyes in incredible detail. He doesn’t have a lot on his phone, because Anna was right, it is a burner cell. But he couldn’t resist showing off a bit the last time he was in the studio. 

“I—wow. Yeah, you’d fit right in at an art school.”

“I’m going to hope that’s a compliment.” 

Mr. Winchester’s mouth ticked up as he chuckled. “You’re really neat, dude.” 

“Thank you.” Castiel said, gruffly. Silence fell over them again as Mr. Winchester took a few more fries. Castiel pushed the plate towards him for something to do. He had to break the tension, “So what do you do at your company?”

Mr. Winchester brushed the excess salt off his hands as he finished off the last of Castiel’s fries. “We do a lot of things. Got our hands in a wide variety of things. But we’ll talk about that later; do you want to come home with me?” 

“I—what?”

“Not-James, painter of Chicago, will you do me the great service of coming home with me so I can fuck you? There’s three hundred bucks in it for you.”

“I—I’ve never…” Castiel felt as if he was blushing furiously while also having all the blood drain from his face simultaneously. 

Mr. Winchester nodded sagely. “I know. But if you’re willing, I’ll make it worth your while. That was what you were after, right? Some rich old guy to pay you to give it up?” 

Castiel considered for a long moment. “Okay.”

Mr. Winchester’s face breaks into that heart stopping smile again, before flagging down the waitress for the check. 

Castiel tries not to smile at the way Mr. Winchester ignores her flirtations the entire time. 

As Mr. Winchester leads them down the road to a huge and shiny black car that just screams ecological disaster, Castiel tries to quell the uprising of butterflies in his stomach. He might be actually taking a dick for the first time tonight.


	2. Ascension (feat. A Lakeside Mansion)

**Summary for the Chapter:**

> Castiel takes a dick for the first time in his life... or not.

Castiel could feel himself dozing off in the car. The engine’s deep rumble under his feet and the soft, familiar tune on the radio made this ride in a stranger’s car seem remarkably familiar. Crap, this was how he died, wasn’t it? Wasn’t this one of his rules, to never go home with a john? Mr. Winchester didn’t strike him as someone eager to murder him, but serial killers often don't look like serial killers. 

The tires raced over something uneven, which startled Castiel out of his reverie. They had turned onto a road, set off from the rest of the city. The coastline came into view, with the moonlight tripping over the waves of the water. In the distance, Castiel could see the pier, with its taller than life ferris wheel, keeping watch over the east side of the city. 

“So, am I gonna get a real name or am I just gonna have to get creative?” Mr. Winchester spares him a glance as the road gets farther away from the bustle of the main streets. They had to be nearing the edge of the water. 

He cleared his throat. “What would have been your creative solution?” Castiel asked, carefully keeping his eyes on the road in front of him. He only looked over long enough to see Mr. Winchester thoughtfully pursing his lips as he thought. 

“Dunno,” he said. “James woulda worked fine, I guess. You look like the kinda guy that has a unique name though, you know? Not like Jeff, or Mark… something cool. Not to pressure you, or anything. If you don’t wanna give me your name… s’cool.” Mr. Winchester started humming off-key to the song on the radio. Castiel wasn’t sure he recognized this one, but he did recognize that Mr. Winchester couldn’t carry a tune to save his life. It was endearing, in a way. This attractive man, who was down-to-earth despite being as rich as he claimed, singing badly was tugging on Castiel’s heartstrings in a way he’d been trying to forget was possible in his current situation. 

“Castiel.” He doesn't know what made him say it. 

Mr. Winchester raises an eyebrow without taking his eyes off the road. “Definitely not what I would have guessed,” he says. “Awesome. Er… that come with a nickname?” 

Castiel shrugged. 

“No nickname? Hmm. Means I get to be the first one to think of a good one then, huh?” Mr. Winchester shot him an easy smile. 

The car careened around a turn and broke out of a patch of trees, into a clearing of road where Castiel could see the water sparkling merrily against the dull navy sky again. Just as suddenly, the road changed again into neat cobblestones, a surface Castiel thought Mr. Winchester wouldn’t allow his prized black car. If the way he spoke about the machine was any indication of its worth, this car had no business carrying plain folk passengers. 

The car coasted to a stop outside of a huge wrought-iron gate, of simplistic bars; thick and heavy enough to suggest force and power, but understated and sculpted enough to show taste. Dean smacked at the visor on his side, grumbling about batteries and someone named Bobby. The gate slid open smoothly, allowing the car to pass, sealing off the rest of the world behind them. 

Castiel wasn’t sure the cobblestones would ever end, but they eventually curved around an exquisite fountain that jutted twenty feet up into the air, and rolled into a paved courtyard. 

He tried to keep his cool, but he simply hadn’t been to a house this large before. The courtyard was surrounded by adobe house on three sides, with a wall of hedges closing off the other side, save for the driveway. An enormous arcade served as the front porch, with clay planters bursting with life sat between each arch. Ceramic tile marked the transition from cobblestone to front door, and looked authentically 18th century, down to the makers’ marks on central tiles. 

“Are you into architecture or something? This doesn’t really fit with the usual style in the city” Castiel said, quirking a brow at Mr. Winchester. The man grinned and ducked his head.

“Nah, I just liked the joint because it was out of the way. Plus, you gotta see the view out the back.” 

“This place is enormous.” 

Mr. Winchester shot him a sidelong glance. “That’s not the only thing that’s enormous, sweetheart.” He grinned even wider when Castiel frowned and huffed. 

…

The way Mr. Winchester threw his keys in a small table in the foyer and toed off his shoes made this impressively ornate house seem much more livable, like this wasn’t for show; this really was the place Mr. Winchester came home to every night and sprawled out on the couch to relax. Maybe he even wandered around in his boxers in the morning, scrubbing the sleep out of his eyes. Castiel got caught up gawking at the Matisse on the wall that couldn't be real, for god’s sake, before remembering himself and hustling into the living room just off the foyer. 

Mr. Winchester stood at a sleek granite bar with a sparking decanter on top, surrounded by glittering cut glass tumblers. Castiel couldn't see the bottle Mr. Winchester was pouring from, but the dark liquid played in the light coming from the chandelier in the center of the room. The furniture in here was all the same cream color, with dark wood accenting. Really, the entire house seemed to be decorated around a central color scheme of extremes. 

Castiel glanced down at the thick rug and down to his shoes. There was a bit of mud on them, and he didn’t want Mr. Winchester’s first impression of him to be that he was messy, along with a smart mouth. He hurriedly bent down to unlace his shoes, and set them by the archway into the living room. He straightened up just as Mr. Winchester turned around.

The man gestured with his glass. “You can go ahead and sit down, it’s not a museum. Want a drink?” The shit-eating grin was back, “You’re probably not of age, but I can make an exception for guests.” 

Castiel tried not to smile, but declined. “I try not to drink on the job.” 

“Suit yourself, but I don’t think we’re ready to strike a deal just yet, are we?” 

“If I’m not mistaken, you said there’d be three hundred bucks in it for me if I came home with you. Are you going back on your terms?” 

Mr. Winchester stepped up slowly to him, “If I’m not mistaken, you said you’d never actually been with a guy before. Is that right?” 

Castiel felt the adrenaline hit his system, heart rate speeding up and palms sweating. His eyes glanced back towards his shoes, and tried to calculate if he could make the front door before Mr. Winchester. Would he need to run? It wasn't often that johns tried to offer him one thing and take another, but it did happen. A night’s wages lost was never worth more than his safety though, and he took pride in his ability to pack up and get out quick. If he grabbed his shoes, he could at least make it down to the ridiculously huge gate before Mr. Winchester could catch him. Perhaps if he was convinced Castiel had already made it out, he would open the gate to come after him, giving Castiel time enough to escape and head the opposite direction of that black monstrosity of a car. 

“Kid, relax, no one’s going to hurt you,” Mr. Winchester held up his hands and stepped back. He set down his glass, and fumbled in his back pocket. He pulled out his wallet, and laid down three bills on the chaise to Castiel’s right. “See, there’s the money, it’s okay. You sure you don't want a drink?” 

Castiel shook his head. His eyes wavered between the money and where Mr. Winchester sank into an armchair, completely relaxed but watching Castiel. He slowly reached out and touched the bills with his fingertips. The bills were crisp and new, not like the torn and crumpled twenty Castiel still had in his pocket from earlier. When he saw that Mr. Winchester was not going to try and snatch them back, he quickly tucked them into the hidden pocket of his jacket. 

He straightened up and squared his shoulders. “So, how do you—uh… want me?” 

Mr. Winchester raised an eyebrow. “Preferably, not looking like you’re about to keel over right there. Why don’t we just take this one step at a time. You wanna sit down?” 

Castiel felt lightheaded, but shook his head. He could do this. It was only a man, and he’d brought plenty of men to their knees before. Actually fucking Mr. Winchester shouldn’t be too much of a stretch. After all, he’d told himself he was willing to do this. Whatever it took. He needed the money, and here it was in front of him. Castiel took a step towards Mr. Winchester where he sat. The man shifted in his seat so that his legs weren’t spread apart, blocking Castiel from his goal. He just needed to—

“Okay, okay kid, take it easy. Please sit down?” Castiel came back to himself and noted how Mr. Winchester was holding himself—like he was trying to keep as much space between the two of them as possible. Maybe he had changed his mind? Maybe he didn't want Castiel after all?

Castiel staggered back and sank down onto the ottoman in front of Mr. Winchester’s chair. He hung his head and tried to get his breathing back under control. What a disgrace. 

Mr. Winchester laid a heavy hand on his shoulder, causing him to pop his head up. Mr. Winchester still had a concerned look on his face, like Castiel was some spooked horse. “Castiel—Cas, I don’t feel comfortable doing anything to you like this. You look like you might be sick,” he tilted his head. “Have you had anything tonight? Anyone give you anything?” 

Castiel shook his head.

“Are you nervous?”

A brief hesitation, but then a nod. 

Mr. Winchester nodded as well. “Guess you weren’t lying about not having done this before, were you?” He stood up and walked over to the bar again, pulling a tall glass out from a bottom cupboard. He filled it from a small sink set into the bar and brought it back to the chair. He held it out for Castiel to take. “It’s just water,” he said. Castiel made no move to grab it. Mr. Winchester waited a few more seconds. “Please, drink it. I insist.” Shakily, Castiel reached out for it and downed it in one gulp. Mr. Winchester sat back on the chair, close to Castiel, but not touching him. 

“So, the way I see it, is that you really need some money, am I right? Probably a better place to live as well?”

Castiel ground his teeth. He wasn’t a charity case, he was a sex worker. Not a very experienced one, but he knew he wasn’t going to make his living anywhere else. 

“Look, I can give you back the money, I’m sorry I can’t—“ he was cut off by a wave of Mr. Winchester’s hand. 

“Not what I meant. Okay, you know how sugar daddy arrangements work, right? I can pay your tuition, your rent, whatever. Money isn't an issue. In exchange, I just want your company. Hang out with me, maybe go to dinner,” Mr. Winchester smiled. “Buy you stuff, that sort of deal.” 

“You want to fuck me?” Castiel felt the words blurt out of him, but felt powerless to stop them. 

The man in front of him licked his lips and looked down. “I can see that’s going to be a thing for you, isn’t it?” he sighed. “I won’t lie to you, I am interested in that, but no way in hell I’m going to do that to you right now. Let’s just take it slow, figure this out, and we’ll see where it goes, okay?” 

Castiel didn’t say anything, but eyed him warily. 

Mr. Winchester nodded and shuffled his foot almost sheepishly. “Yeah, I’m a sleaze.” He frowned and his eyes turned speculative. “I find it hard to believe no one’s ever offered you this before.”

“I mean—I have… once… but I ran before the guy could get very far.” Castiel shrank back into himself. 

“Well, here we are. I’ve got the money and you need the help.” Winchester gestured around.

Castiel was silent for several moments. “Just like that? I just have to—to ‘hang out’ with you?” He still had trouble grasping exactly what was expected of him.

Another small smile stole across Mr. Winchester’s handsome face. “Just like that.”

Castiel’s eyes narrowed. “This seems too easy.” 

Mr. Winchester huffed a sigh and rolled his eyes. “It’s not supposed to be a hardship, Cas. It’s a mutually beneficial relationship here. Symbiosis. You could have picked candy as your payment and you’d be swimming in the stuff.” He shrugged.

“Tuition, art supplies, all that stuff…?” Castiel heard the calculation in his voice and didn’t want Mr. Winchester to think he was so quickly turned around by the prospect of payment. Sugar daddies who thought their babies were only in it for the money usually wound up dumping the poor gold-diggers after a week or two. 

“Trust me sweetheart, you’re never gonna have to buy another paintbrush or canvas again. I’ll get you what you need.” Mr. Winchester stood up and stuffed his hands in his jacket pockets, still impeccably put together at the late hour in his leather jacket. “And you know what I want, so… it’s yours if you want it.”

“Do I have to live with you?” Castiel asked, half fearfully. He really didn't want to end up a kept houseboy, waiting for Mr. Winchester to return in the evenings. Maybe he wouldn't even be let out of the house except for school like a prisoner. What would Anna say? 

“Do you want to?” Mr. Winchester kept his cool, collected demeanor. He didn’t say it with any inflection that suggested he was trying to sway Castiel either way. 

Castiel hesitated. “I… don’t know.”

The man nodded. “We can always hash that out later if you want.” 

“Do I have to call you ‘sir’?”

Mr. Winchester laughed out loud. Castiel thought he looked impossibly more attractive when his face lit up with joy, even though it felt like looking into the eyes of a great white shark or a tiger. “You get off on that?” Mr. Winchester asked. Cas shrugged. “Call me whatever you like. I can go by Mr. Winchester if that makes you more comfortable.” Mr. Winchester looked up thoughtfully, “Personally, I like Dean better. Makes me feel less old, but—up to you.” 

“Dean, then.” 

“Pleased to meetcha, Cas.” Dean smiled. 

A moment of silence passed between them. “You’ll have to show me what you want, I don’t know what I’m doing.” Castiel leaned forward, halfway looking for reasons for the man to back out of his offer.

Mr. Winchester’s eyes gleamed with a look that sent an involuntary shiver up Castiel’s spine. “Believe me, sweetheart, I’ll take real good care of you if you let me.” Mr. Winchester pulled his phone out of his pocket, glanced at it, and shook his head. “It’s real late, Cas. I’ve got a spare room you can use for the night if you want to hang out for a bit. We can talk about this more in the morning if you want.” When Castiel hesitated, he added with a sad smile, “I promise no funny business… unless you ask.” He finished with a goodnatured leer. 

“Let me just text my roommate… can I—tell her where I am?” 

Dean widened his eyes. “Oh, there’s a roommate? Yeah, feel free, lemme write down the address for you.” He scribbled something down on a piece of paper that he handed to Castiel. “I’m going to go get your room set up, just come down the hall when you’re done.” 

He disappeared down the long hallway just off the room, also paneled in dark wood. Castiel felt glad for a moment alone to gather his thoughts. 

_> > Sent:_  
Not coming home, at a friend’s. 

Castiel hesitated before typing “friend,” because he really wasn’t sure what to call Dean at this point. It was easier than calling him “my potential sugar daddy” though, and far more stomachable. He immediately turned his phone off after sending the message. It wasn’t safe, and Anna would beat his ass for making her worry, but he couldn't stand the thought of anyone else in his head right now. 

He took a few deep breaths, and turned down the hallway, looking for Dean. There were many doors on either side of the hallway here, but they were all closed, preventing Castiel from seeing inside. The walls were dark, but the same plush cream carpet from the living room was in here, and bright ceiling lights hung every few feet. One door was open near the end of the hall, to the right of a large set of double doors with heavy bronze handles. He peeked into the open door and saw Dean pulling back a set of heavy-looking curtains onto a view of the Chicago skyline that Castiel was fairly certain he’d seen on a postcard once. 

Castiel cleared his throat to announce his presence. Dean turned and an easy smile spread across his face. 

“Heya Cas. Hope this is okay, at least for tonight.” 

It really was. The bedroom was as simple as the hallway. The bedding was plain white and the bed frame and headboard were black. The entire west wall was made of glass, leading out onto a small balcony, and into that picturesque view. Black and white prints hung on the walls, far enough apart to look like a gallery. A door stood partially ajar against another wall that led to what Castiel assumed was a bathroom, as a large wardrobe served as a closet. 

Castiel wasn’t sure he’d ever had this much room to himself in his entire life. He walked further into the room and joined Dean at the window.

“I brought you something to sleep in, I know we didn’t stop to grab any of your stuff, so…” he palmed the back of his neck bashfully. He gestured to the bed. “It’s memory foam, so you should be comfortable, and there are extra blankets in the closet. I’ll let you get some sleep.” Dean padded to the door. 

“I’m down the hall if you need anything, the double doors at the end. My housekeeper, Missouri has the night off, so don't hesitate to wake me up.” He started down the hallway, only to pop his head in once more. “Oh, and the door locks… meant to tell you that.” He disappeared again with a wink. 

Castiel gazed after him for a second, before crossing the room to the door and sliding the heavy lock, which clunked satisfyingly. He then trudged over to the bed and fell down on it face-first. He didn’t remember it, but he fell asleep within seconds of landing.

**Notes for the Chapter:**

> I guess the "or not" was more accurate... 
> 
> Next update will follow soon after, because I can't stand leaving it this way.
> 
> -azo


	3. He's My Collar

**Summary for the Chapter:**

> Castiel wakes up and takes a test-drive.

Castiel was staring up at the ceiling for far longer than he recognized being awake. He wondered how many times Anna texted him last night after he turned off his phone, or if she had given up and started calling. He hadn’t ever not come home after a trick. It was part of the rules; you don’t go home with the john and definitely never go anywhere without telling someone else. Here he was in the expensive lakeside estate of a man who wanted to keep him as a live-in boyfriend in exchange for paying for school. There had to be a catch; this was the kind of deal sex workers combed the city for. Even more, his potential sugar daddy seemed… good. He wasn’t concerned that Castiel hadn’t been with a man—or anyone—before, and seemed encouraged by it. He could be one of those guys that got off on the whole virginity facade. But, Castiel reasoned, Dean was interested before he knew that fact about him. 

A quick rap at the door made him jump. He threw the covers off of his body and hastily scrambled to the door, supremely aware that he was still in the clothes Dean had laid out for him. He woke up last night in a fit of strange dreams and changed into more comfortable clothes, before swaddling himself in the plush comforter and trying for a few more hours of sleep. 

A kind-looking woman stood at the threshold when he opened the door. She was pleasantly round and had her hair smoothed back by a headband. 

“Good morning Castiel, Mr. Winchester wanted to know if you would like to join him for breakfast?” Her voice was lilting and melodic with a slight southern accent

“Uh… yeah—lemme just…” he glanced back at the bed, which was still a mess, and his clothes from the previous day. 

“You’re fine just as you are; Mr. Winchester is still in his PJs.” She beckoned him out into the hall and started leading the way back through the main room and down another hallway.

“Mr. Winchester couldn't come get me himself?” Castiel wondered out loud. The woman chuckled.

“Of course, I had to see his new friend for myself, sugar. My name’s Missouri. I do all of Mr. Winchester’s cooking and cleaning.” 

“You clean this entire place? It’s huge.” Castiel marveled. 

Missouri glanced over her shoulder. “Mr. Winchester doesn’t trust too many people. Just me and his uncle Bobby anymore around the house.” She pursed her lips like this was a subject she didn't like to talk about. She pulled Castiel into the kitchen, which was all sparkling stainless steel and black granite. An older man sat at the breakfast bar, occasionally surfacing from his newspaper to drink from a cup of coffee. Dean stood at the stove in boxers and a threadbare t shirt, flipping pancakes around and generally making a mess. Even from the back, Dean looked like the pages of a male lifestyle magazine come to life. Castiel wondered how much money one had to make before everything you did became attractive. 

“Dean, I told you to watch yourself when you’re measuring, boy!” Missouri tutted and immediately grabbed a paper towel to clear the spill by the sink that Dean had managed to cause while she was away. Castiel raised his eyebrows at the familiar way she addressed Dean. The older man at the bar shook his head fondly as Dean protested and had the spatula taken away from him. Missouri directed Dean to sit at the bar and instructed Castiel to sit down next. Castiel hurried to obey, he got the feeling that Missouri wasn't used to seeing her orders ignored. 

Dean leaned his elbows on the counter and let his feet dangle from the high stool. “Good morning, Castiel. Sleep well?” He took a sip from his coffee mug. 

“I couldn’t figure out your space blinds, so I was quite literally up with the sun.” Castiel replied, a little cooly. Dean already knew what he was getting into, if he didn’t want his staff to know the specifics of his personal life, maybe he shouldn't invite his potential sugar babies to breakfast out in the open. 

Dean chuckled, however, and elbowed the bearded man next to him. “See, Bobby, I told you he’s a firecracker. And he paints.” 

The man, Bobby, huffed and lowered his newspaper a bit. “Well, good to know you finally made some friends with personality.” He took a sip from his mug and put the paper back up, like that was the end of the conversation. 

Everyone kept calling him Dean’s friend. Did they know why he was here? Did they suspect anything about why a strange man was suddenly in their guest room as if nothing was out of the ordinary about it? 

Castiel’s thoughts were interrupted by Missouri setting a huge stack of the fluffiest pancakes Castiel had ever seen in front of him. She graced him with a kind smile before setting an equally huge stack in front of Dean. 

“Remember to chew with your mouth closed, boy. You’ve got company.” Missouri said, raising an eyebrow. Dean stuck his tongue out at her childishly and got swatted for his trouble. Castiel smiled down at his plate when Dean nudged him playfully, tucking in eagerly. 

Bobby, Missouri, and Dean talked amicably over their breakfasts, making conversation about their plans for the day, like a normal family, like there wasn’t an extra guest at the table who gave blowjobs for spare cash in the back alleys of Chicago. Castiel would feel like he was intruding, but Dean made sure to include him as well. Missouri, who Castiel got the feeling was more like a mother to Dean than a housekeeper, asked if he was in school and he talked for a bit about his projects for class. Dean paid attention the entire time like he was genuinely interested in what he had to say, and even asked his opinion on the Paul Gaugin exhibit in the Field. 

“I mean, I’d like to go,” Castiel started, “but I still have a bit of moral dilemma over the subject of his work—his wife was a child. Why do we still gratify pedophilia in the traditional arts?” He kept going, until he realized that this might not be the best breakfast conversation, but Missouri was nodding along with her eyes wide like she agreed, and Dean looked thoroughly entertained. 

Castiel wondered again to himself how often Mr. Winchester brought home “friends.” Maybe Bobby and Missouri treated this situation so… normally, because for them it was. Perhaps Dean did this sort of thing all the time, and it had become a part of their routine. 

Breakfast ended with Missouri fretting about the state of greenhouse faucet—“Bobby, it won’t stop doing that thing and you’ve fixed it about four times!”—while clearing everyone’s dishes, except Dean’s. Castiel moved to help at the sink, but was grabbed by Dean and pulled to safety before Missouri’s hand could swat his for trying. 

“I just don’t understand how you can break that damn thing at least three times in a week?” Bobby grumbled to himself as he put his empty mug and plate in the sink, trudging out of the kitchen with Missouri on his heels. Dean shook his head and mopped up the last of his syrup with a bit of pancake. 

Castiel swallowed and worked his jaw for a few seconds before speaking. “Do… do they—Bobby and Missouri— know why I’m here?” 

Dean looked up at him. “They know that I brought you home for a reason. They don't know why exactly, and they don’t need to know. They’re good about leaving me to my business and right now, you’re my business.” He grabbed his plate and deposited it in the sink. He snagged his coffee cup and refilled it, sitting back next to Castiel. “So, no. They don't know exactly why you’re here, but they’ll be good to you while you are.” 

“So keep it cool around them?” 

Dean smiled dangerously over the rim of his mug. “Only if you’re plannin’ on makin’ a deal with me, Cas.” 

Castiel flushed. “Can I ask you a personal question? You don’t have to answer if it’s too… much.”

Dean shrugged and stuffed the last of his pancake into his mouth. He grabbed the paper that Bobby left and leafed it open. He bypassed the other sections and went straight for the comics. 

“Why do you…do this. Why do you want this kind of—of relationship with me?” 

Swallowing his mouthful, Dean held up his fingers and started ticking them off. “Well, you’re pretty cute, and you said you got scholarships for school, so you’re pretty smart… for an idiot who tried to get a john in a dive bar, and you got a bit of an attitude, which is cool.” He shrugged. “I dunno, man. It’s a business transaction. I’m the businessman who gets to pretend someone like you would actually want to spend time with me and all I gotta do is pay some bills. Pocket change.” He chuckled to himself as he turned a page.

“But you’ve gotta know you can get anyone you want without paying for it.” Castiel said it and snapped his mouth shut. He hadn’t meant to imply that he wasn't worth Dean’s time, just that the sugar daddy community wasn't well known for its attractive and eligible bachelors. 

“Yeah, but you’re a lot cooler than anyone else I’ve met, so…” He waved his hand. “Plus actual relationships take time. And commitment. I don’t have the patience or the sanity for either of those things. Seriously, if there’s one thing I’ve learned, it’s that why bother with taking the long route, if you can just pay for a roundabout?” 

“What is it you do, again?”

Dean waved his hand again, dismissive. “A lotta stuff with Amnesty International. We get good people out of bad situations.” 

“So nice to know that AI gets by on the shortcuts…” Castiel said, dryly. 

Blinking at him, Dean looked up. He let out a sharp bark of laughter. “See, that’s why. You got a major attitude. S’cute.” 

Castiel opened his mouth again, but Dean stood up. 

“I gotta get to a meeting, but can we talk about this when I’m done? It shouldn't be more than an hour or so. You good here or do you got somewhere you need to be? You got a job during the day?”

Castiel stuttered. “I-I mean I can't stay here, can I?”

Dean shrugged. “As long as I’m not keeping you from anything, right?” Castiel shook his head. He should probably turn on his phone again to see if he could control the hurricane that Anna no doubt managed to stir up. Going home now would shatter this illusion, though. And for now, it was one that Castiel wanted to keep alive as long as possible. “Yeah, stay here then, it’ll be great! You can watch whatever you want on tv and Missouri can make you whatever you want to eat. And then we can talk when I get back, alright? Promise.” 

Castiel hesitated for a moment before nodding. He was treated to watching Dean’s face split into a grin like the sun was coming up over the horizon. Dean pecked him on the cheek, before clapping him on the shoulder and leaving the kitchen, humming a song vaguely off-key. Castiel put a hand on his cheek, which felt very warm. He whipped his hand away and balled up his fists, determined not to let his day turn into a bad rendition of Pretty Woman. 

He glanced around the empty kitchen for a while before wandering back down the hallway where Dean had gone. He turned a corner and found himself in another living room, different from the one he was in last night. This room faced northeast and had a huge flat screen television mounted across the room. He could see Missouri and Bobby outside, seemingly arguing and gesticulating with hand tools while they pointed at the greenhouse. Castiel would like to see it sometime. If the greenhouse was as well-kept as the rest of the house, Castiel was sure the flowers were wonderful. He settled in on the sofa and rooted around for a remote. The only thing that vaguely even resembled a remote was a device about the size of an iPad sitting on the coffee table. He picked it up and hit the green power button in the corner. The screen lit up with several options. ‘Watch TV’ was highlighted but more options that Castiel knew what to do with were available. Stupid rich people and their space televisions. Hesitantly, Castiel selected his way through several options before he got to a program he recognized. He settled in to watch an episode of some show he remembered his sister watching years ago in a different life.

Castiel’s family was off-limits for conversation pretty much always. He didn’t like to talk about his home life, and didn’t like others to ask about it. All he said was that he had a mother and sister in Pontiac, and that they didn’t see much of each other anymore. No father, no school friends. Anna was the first person he met off the bus to Chicago, and the only friend he kept in contact with. Apart from her, Castiel had no one to tell where he was, no one to marvel over and laugh at the ridiculous but understated opulence of his current surroundings. He wasn’t expected at the bookstore until Monday afternoon, and the Institute was on break for summer term. 

He really was quite alone. 

Standing and going to the window, he saw that Bobby had left where Missouri was standing and had gone to use the riding lawn mower on the grass on the other side of the greenhouse. Castiel chuckled that he could see Bobby’s grumpy expression from here. He accidentally caught Missouri’s eye where she was trimming the peonies around the trees. She waved pleasantly, and Castiel had to force himself to wave back, instead of ducking out of sight like he wanted to. Missouri was definitely one of the nicest people he had met in Chicago, but she was also one of the most intimidating, in a strange way. 

He sat back on the couch and tried to distract himself with the show. Even though he had slept quite comfortably the night before, he let his head drop against the armrest of the sofa and drift off with the show playing mindlessly in the background. 

…

“Cas… Cas! You look less grumpy when you’re asleep, you know that?” 

Castiel woke up slowly, groggy from sleeping in the middle of the morning. Dean stood over him, smiling down and looking ready to take over several Fortune 500 companies in his dress shirt and tie. 

“What time is it?” Castiel sat up. Missouri was no longer outside, but Bobby was still maneuvering a riding lawn mover past the window over the extensive grounds. 

“About 11:30. Told ya I’d only be gone about an hour or so.” Dean dropped a suit jacket across the glass-topped coffee table and sat heavily in a chair across from Castiel, propping his feet up on the tabletop. “You still wanna talk?” 

“I don’t know where to start, to be honest.” 

Dean’s mouth lifted in an understanding smile. “It’s kind of a lot, I know. But it’s something I enjoy and I think you could really benefit from it too. Money or not.” 

Castiel raised an eyebrow. “You think I would benefit from someone paying me to pretend to be his boyfriend or his—his virgin experiment?” 

“I think you’d benefit from someone more… experienced calling the shots for a while, at least in this situation.” Dean steepled his fingers and mirrored Castiel’s expression back at him. He was acting the part of a hard-hitting negotiator, Castiel could tell. 

“I can’t handle myself?”

“I don’t think you want to.” 

Castiel was silent for a moment, and Dean smirked like he already won. 

“You don’t know a thing about me or what I want.” Castiel could feel his fingers digging into the upholstery.

“I’ll make it my business to know.” 

“Like a dom. And I’m your sub.” 

Dean gazed at him speculatively. “What do you know about dom/sub relationships, Cas?” 

“I don’t know if you’ve noticed, Mr. Winchester, but I don’t particularly take well to being ordered around.” Castiel knew this wasn’t the way to get Dean to like him or get him to want to help, but there was something about this man that made him want to push back. To see how much he could get away with and still make Dean laugh. 

True to form, Dean cracked a smile. “In a very watered-down, skewed sense, I guess there will be some ordering around. Did ya get that from a tv show?” 

“Dean—“ 

“Alright, to be fair, I’d be real worried if you knew how to sub right away before you even knew how to take a dick, man.” 

Castiel felt a brief flutter of panic in his chest again. “Maybe this isn’t the best idea, Dean. You probably don't want to mess around with me when I have no idea what I’m doing.” 

“It’s not messing around if I fully intend to take care of you.” Dean said, a patient expression on his face. “But I also don't want you to feel pressured into doing this if you don't want to. It’s very important that you’re able to choose this of your own free will.” He leaned forward, assessing Castiel with his eyes. 

Castiel sighed, trying and failing to stop the small smile on his face. “What do I have to do?”

“It’s a relationship of trust. The dominant, that’s me, is basically in charge of the submissive, that’s you. Now, that can mean doing what I tell you, but it’s more than that. As the dom, I make sure you’re kept safe at all times, no harm will come to you unless you wish it, and I pay attention to what you need. You trust me with control over the situation, to make sure it doesn't get out of hand and that nothing that you’re uncomfortable with happens. And of course, I trust you to tell me when it gets to be too much, provided I don't notice sooner.”

“What if something happens if… when we’re…” Castiel gestured vaguely between the two of them.

Dean’s eyes hardened. “Even if it happens in the middle of a scene— no, especially if it happens in the middle of a scene, you have to tell me and I’ll make it right. But that’s the kicker. I’m trusting you to tell me when to stop. You can’t let me go further than you’re willing to go, because then it isn't fun anymore. Understand?”

“But you’re in charge?”

Dean leaned back. “That’s the beautiful thing, Cas. As the submissive, you really got all the power here. You can tell me when to stop and I’ll stop. All I’m doing is taking the control and directing it in a way that lets you sit back and enjoy.”

Castiel sat up straighter on the couch, still wary, but getting used to the idea.

“Wanna take a test drive?” Dean’s eyes were positively glowing now.

“I—I don’t…” Castiel fumbled, glancing at the window. What if someone saw? 

“Relax, we haven’t even gone over the paperwork yet to make it official.” Dean stood up and undid his tie.

“There’s paperwork?”

“I like everything in writing.” Dean tossed the tie over the arm of his chair and started undoing the buttons of his shirt. He stepped out of his shoes and draped the shirt over the chair as well. His chest muscles rippled with the motion, causing Castiel to suck in a breath. Dean’s biceps alone made Castiel want to hang on to this man for the rest of his life. His stomach wasn’t as defined as Castiel might have thought, but there was no mistaking that the man in front of him was packing a truly frightening amount of muscle. 

Castiel stared. “D-Dean— Mr. Winchester, what are you doing?”

The man smiled and it felt like being trapped in snake’s sights. His voice was smooth as whiskey, lowered a few notches to an intimate volume above a whisper. “Just take it easy. Right now, I want you to be the dominant. Just for a bit. See if you wanna give this a whirl for real. Is that alright?” Dean knelt in front of Castiel’s chair, just in front of his knees. Dean’s proximity made the room feel a hundred times hotter. He looked up at Castiel from underneath his lashes. “What would you like me to do, Castiel?” 

Castiel’s knee twitched. He felt jittery. He knew exactly what he would like to ask Dean to do. Knew he wanted to let this man suck him off. He’d never had a blowjob before; he’d given them plenty of times, but not one guy had ever bothered to reciprocate. “I can ask for anything?” Castiel’s voice sounded shaky to his own ears and he hated it.

Dean leered, his perfect teeth barely showing. “Anything. I don’t have a lot of rules because I basically like everything. But if we run into something I don't like, I’ll say ‘funkytown’. Got it?” 

Castiel nodded and had to take a few moments and breathe, his palms were so sweaty. Dean chuckled at him, his expression widening into a filthy smirk. Castiel cleared his throat. “Take off your pants.” 

The smirk transformed into an outright salacious grin as Dean stood up and slowly lowered the zipper of his black slacks. Castiel thought idly that Bobby could drive by any minute and see them in the living room like this. But it didn't seem to perturb Dean at all. Castiel was transfixed as Dean pulled his pants down his muscled legs. It seemed that he was built… well, all over. Castiel felt himself harden in his pants and he automatically moved to cover himself. He was stopped by a forbidding sound from Dean.

“Don’t be ashamed of this, Cas. It’s meant to make you hot. You still good or do you want me to stop?” Castiel blushed hotly and shook his head. Dean waited until he dragged his hands away from his crotch before continuing. Dean stepped out of his pants and swept them to the side with his foot. He pulled his socks off next. When he straightened up, Castiel could see the outline of his erection through the thin cotton of his black boxer briefs. He palmed himself a few times before placing both hands behind his back. Castiel felt his breath catch. 

It took a few seconds for Castiel’s gaze to wander back up to Dean’s face, but he saw that smirk again before it was quickly schooled into an expectant, but patient expression. Dean was waiting to be told what to do next. Dean would do whatever Castiel told him to do. He could order this man to suck him off and he would. Probably with a smile on his face. Castiel sat up straight in the chair. “And your underwear.” He was proud that he mostly kept the tremor out of his voice.

Dean grinned again, his eyes flashing as he turned around and slid his boxer briefs down over the curve of his ass. He bent down as he slid the underwear down, giving Castiel a show, like he knew he was attractive.

And what a show it was.

Castiel had never really considered himself an “ass” man. He didn't understand why the guys in his year got so worked up whenever the cheerleaders walked by in their short skirts on uniform days. But maybe, if those asses had the same appeal to their viewer as Dean’s ass had to Castiel… maybe he understood a little. 

Dean’s ass was breathtaking. It was muscled and round in a way that suggested Dean did a lot of heavy lifting, with smooth, pale skin. Dean was doing the world a huge disservice by wearing clothes during the day. With his underwear on the floor next to his pants, Dean turned around slowly, one eyebrow cocked like he was waiting for Castiel to say something. His cock hung proudly between his legs, thick and hard. It was only at about half-mast, but Castiel could tell when Dean was fully hard, his cock was definitely something to write home about. Castiel’s mouth dried up in two seconds flat. 

“Need some help there, Cas?” Dean’s voice was low and gravelly. Castiel instinctually pressed his knees together when his erection reached a point of straining against the material of his pants. 

“Blow me.” Castiel breathed, a surprise to his own ears. His gaze skittered from Dean’s erection to his face where Dean could barely keep the smugness off his lovely face. 

Dean knelt to the ground again, shuffling in between Castiel’s knees so that his calves bracketed the man in front of him. With his legs spread slightly like this, there was no way Castiel could hide the fact that he was very turned on by the mere act of Dean taking off his clothes.

“Is that all you want?” Dean asked, almost innocently, eyes wide. His gaze never left Castiel’s, but his hands swept up Castiel’s thighs, causing little snakes of sensation to fizzle all over Castiel’s skin, up to his hair. 

“G-get me hard with your mouth and then r-rub your cock against mine.” He said, blushing at his own stammer. God, could he sound more like a virgin?

“That’s more like it.” Dean grinned. “Can I take off your boxers… jesus, my boxers?” 

Castiel nodded hastily and lifted his hips when Dean pulled his boxers down in one smooth motion. His cock slapped against his stomach and had a smear of precum right at the tip. Dean licked his lips as he looked at it, causing an involuntary whimper from Castiel. Dean leaned in slightly, but looked up at Castiel for an order. He was so close that Castiel felt Dean’s hot breath on the head of his cock and it made him shiver. He needed to get that mouth on him as soon as possible. 

“For fuck’s sake, Dean. Please, blow me.” 

Dean quirked an eyebrow and ran the flat of his tongue over the head of Castiel’s cock. He swirled around the tip and pulled off enough to suck wet, lush kisses down the underside, following the same trail as he licked back up. 

Castiel threw his head back and whined. Nothing had ever felt this good and Castiel was inclined to believe that nothing would ever feel this good again. He looked down again to catch Dean still looking at him, drinking in his facial expressions and managing to look snarky and happy around Castiel’s cock. Dean’s hands crept up over Castiel’s knees and inched up his thighs. Dean’s fingers tightened and spread his legs apart a bit more, allowing Dean more access. For an entire second, Dean pulled off entirely and asked Castiel how he was doing.

“Oh my god, Dean. Don’t stop.” He gasped. Dean grinned, absolutely filthy and took all of Castiel’s cock down his throat. Castiel keened for it, wondering at the last second if it was bad to thrust into Dean’s mouth, not wanting to risk Dean stopping. Castiel felt Dean’s hand grope for his and for a wild second, he thought Dean wanted to hold it while they were connected like this. But Dean grabbed his hand and dropped it on the back of his head and looked up at Castiel again, willing him to understand. Castiel threaded his fingers through Dean’s hair, softer than he would have guessed, and pulled lightly. Dean’s eyes closed briefly around a hollow moan which did things to the way Dean was touching Castiel right now. 

Castiel was a wreck. He felt like he should be more ashamed of how loud he was being, but he couldn't find it within himself to care. This was perfect. Dean was perfect. He never wanted this to end.

And then it did.

Dean pulled off of Castiel entirely and Castiel quickly withdrew his hand from Dean’s hair, afraid he had done something wrong. But Dean simply straddled Castiel where he sat on the big chair, folding his legs up on either side of Castiel’s lap. This new position brought Dean’s cock in direct contact with Castiel’s, and only then did Castiel remember that he had technically given Dean a two-part order. Dean’s hair was a mess from Castiel’s hand in it and his eyes had a feral look about them, like this was somehow doing as much for him as it was for Castiel. Castiel wasn’t sure how that was possible, as he was sure he was ruined for anything else for the rest of his goddamn life. 

Dean reached for Castiel’s hands again and placed one directly on Dean’s magnificent ass, at which point, Castiel had to physically will himself to keep it together, and the other on Dean’s hip. 

“Need you to touch me.” Dean ground out and sank down so Castiel could feel every wonderful inch of Dean’s cock against Castiel’s own. For this kind of friction, Castiel reckoned that Dean could ask him for anything, and he would do it. Dean brought their foreheads close together, one of Dean’s big hands behind Castiel’s head, pulling him in. He started rocking in Castiel’s lap and Dean’s hitched breathing was soon drowned out by Castiel’s whimpering sighs with every thrust of Dean’s. Castiel grabbed a handful of Dean’s ass and thrust upwards as best he could, wanting as much contact as he could get. He tried to speed them along, feeling his orgasm coming fast but every time Castiel would get almost close enough, Dean would slow down. Castiel felt his abdomen tightening up. Everything was narrowing down to the places where Dean’s hot skin was touching Castiel’s.

Castiel was on the verge of losing his mind. He was sure he must sound positively stupid with the breathy sounds that were leaving his mouth. Dean seemed eager to catch them all though, he didn't stop staring at Castiel at all. Castiel had to close his eyes to keep it together, to keep from losing his mind entirely, but Dean kept his gaze trained on Castiel’s face. Their faces were close enough to kiss each other, but Dean did not. Castiel wanted the heat on his face and lips like the heat from Dean’s mouth this morning, when he kissed him before he left for work. It seemed like Dean wanted to kiss him, but he was restraining himself, almost as if he was waiting for—

—oh. 

“K-kiss me?” Castiel asked, hesitant. Was this allowed? 

Dean growled and brought Castiel’s mouth crashing to his. His tongue immediately sought entrance in Castiel’s mouth, and Castiel opened eagerly for him. Castiel’s meager experience with kissing had never involved this much heat. There was the heat from Dean’s palm on the back of his head, holding Castiel to him while he ravaged his mouth desperately. The heat from his other hand, tipping his chin up how he wanted it and splaying across his throat. The overwhelming heat of Dean’s mouth against his. And of course, the heat spiraling up from where he and Dean were touching, all the way up to the top of his head.

Dean’s thrusts were speeding up and losing regularity. He seemed to be close to losing it, close to the level where Cas had been simmering for what seemed like forever. Castiel ran the hand not groping the hell out of Dean’s ass over his abdomen, reveling in the way the muscles jumped. Feeling brave, he moved his hand down and closed it around both of them. It felt strange, having two cocks in his hand. It was slick from both of them leaking precome and about as hot to the touch as his skin felt. He stroked once, twice, and felt himself topple over the edge. He groaned into Dean’s mouth and Dean pulled back to watch him lose it, keeping his thrusts regular, working him through it. 

Cas’s head swam, there was so much pleasure and fire coursing through his entire body. He let his head hit the chair behind him as his body seized up, painting his stomach with white. He noticed Dean was still thrusting desperately against him and without thinking, he closed his fist around Dean’s cock once more. Dean dipped his head to rest against Cas’s shoulder, panting. 

“Please, Cas. Finish me off.” Dean groaned into Castiel’s skin, punctuating with a sharp press of teeth. Castiel kept going, greedy to make Dean come, eager to see him fall apart. It didn't take too long, a few more strokes saw Dean stuttering into Castiel’s fist and tensing up, his body a long line of taut perfection. He groaned into Castiel’s shoulder before biting down again on the skin there, causing Castiel’s hips to jerk mindlessly. More white joined Castiel’s release on his stomach as Dean thrust against him, riding it out. 

They were left panting on the chair, skin sticky between them. Dean raised his head to look at Castiel, lips slipping lazily across his neck. 

“What did you think? Not too bad, eh?” Dean asked breathlessly. Castiel laughed, just as out of breath. 

“Is it always like this?” He wondered.

Dean slowly got up and reached down for his underwear, which he used to clean his and Castiel’s stomach before tossing them in the heap with his pants again. “Not always.” He said, truthfully. “This was definitely a positive though, I’ll tell you that.” He grinned at Castiel, almost shy. He walked over to where the bar was and poured himself a drink.

Castiel stood up and pulled his pants up, groaning at the soreness he felt from having been tense for so long. “And you prefer to be the one doing the ordering around?”

Dean shrugged. “I’ve been both. I dunno, sweetheart, there’s just something about you that’s got ‘submissive’ written all over your face though.” He shot a wink as Castiel before taking a drink, still completely naked. He set the glass down on the coffee table and turned his full attention back to Castiel, his arms out to either side.

“Whaddya say, Cas? You wanna make a deal?”

**Notes for the Chapter:**

> Maybe I shouldn't have done this... I don't want to get your hopes up to expect updates so often... whoops. Imma try for every week on Sunday afternoon for an update. Let me know what you think in the meantime? 
> 
> Chapter titles come from whatever song I have playing at the moment. For some reason, my playlists have just been really in tune with my story... 
> 
> -azo


	4. Show Time

**Summary for the Chapter:**

> When everything gets to be too much, you need some fresh air, a cup of tea, and maybe some skeevy bar bathroom propositioning to make it better...
> 
> Content warning for mildly dubious consent that is realized and dealt with promptly.

“What’s watersports and what does that have to do with sex?” Castiel looked up from the list of things that Dean deemed unacceptable for their arrangement. He was relatively relived to see ‘rape play’ and ‘humiliation’ on Dean’s list of limits that he would not concede to perform.

Dean grimaced without looking up. “I’m not really keen on it… at all, so if you don’t know what it is, let’s just leave it at a hard limit.” He was fully clothed again, something Castiel was a bit disappointed about. He sat on the opposite side of a truly ridiculous mahogany desk. It was almost completely clean except for an errant stack of post-its that Dean kept doodling on, ripping off the top one, and tossing into the trash bin beside the desk. 

Dean had drawn up a rather exhaustive list of everything he claimed to either be willing to negotiate trying with Castiel or that “under no circumstances was Castiel to even suggest.” A row of blank lines underneath were supposed to be for Castiel to list what he was interested in, specifically, and things he wanted to avoid. He quickly added ‘watersports’ to his “Not Interested” category. If Dean didn’t like it, Castiel was sure he wouldn't either. 

Some were easy to consider. ‘Dirty talk’ was the first thing that made it onto his “Interested” list, he could only imagine what the sound of Dean’s voice could do to him. The first was followed quickly by ‘blow jobs (giving/receiving)’ and ‘frottage.’ Some needed explaining. 

“Breath control?! Like you’re going to choke me? That’s fun to you?” Castiel gripped his pen so tight, he thought it might break.

Dean glanced up and smirked at his expression. Slowly, he stood up and walked around the desk, hands in his pockets. Head held high, and surveying him with an easy regality, made Castiel feel small and he instinctively drew his arms in a little tighter to his torso. Dean eased himself into Castiel’s space so his hands rested on the arms of Castiel’s chair. Castiel felt his eyes widen and he drew in a breath. Dean smelled delectable. Spice and musk with a warm undertone that Castiel could not name. 

“Can I kiss you and show you how it’s done? I’ll be gentle, I promise.” Castiel felt himself nod and his tongue snaked out to wet his lips. Dean tracked the motion and leaned in ever so slowly, giving Castiel all the time to refuse him. Warmth spread through Castiel’s body at the thought of being connected with Dean’s once again, his mouth opening when Dean’s tongue traced against the curve of his bottom lip. This was easy. This was good. Kissing Dean was the easiest and best thing in the world and Castiel tried to follow his mouth when he pulled away minutely. A big, warm palm slid up his chest and up over his throat, pushing him back a little. Dean’s hand pressed right over his Adam’s apple, causing his breath to hitch a little. Dean’s mouth sought out his again, keeping his kisses light and undemanding. Castiel felt a little more pressure against his throat, enough where he heard a hollow sound when he tried to breathe. Panic flooded his system, making him jerk under Dean’s hands. Carefully, Dean pressed forward and kissed him again and Castiel couldn't find it within himself to fight. He melted into it, moaning softly when he started feeling slightly dizzy. He pressed forward against Dean’s palm but before he knew it, Dean had backed off and his hand was removed from Castiel’s throat. Muggy stars swam in his vision until it cleared and he coughed slightly. 

Dean watched him attentively. “Maybe we should have set up a safe word for you earlier, if I knew we’d be doing a practical demonstration.” The corner of his mouth lifted slightly. 

Castiel considered. “That was… interesting. Good. I don't know if I’d want that all the time, but it was definitely… different.”

Dean’s gaze grew heated. “You were so good, too. Kept reaching forward for me… I’d be happy to do that again if you liked it.” 

Castiel added it under his “Interested” column. He cleared his throat and addressed the next item on the list.

“So… bondage?” He turned it into a question, looking up expectantly at Dean. 

Dean smirked and sat on the edge of his desk. “Bondage.” He answered simply. 

“You want to tie me up and… what? Whip me?” 

Dean shook his head. “Not quite. I’m not a huge fan of flagellation, but I’ve done it before, if you’re into it.” He winked as Castiel flushed red. “Nah, what I’m into is tying you to the bed so you can’t move unless I want you to and having my wicked way with you until you’re begging me to fuck you properly.” Castiel shifted in his chair and Dean raised an eyebrow. He stepped forward, pressing into Castiel’s space and forcing him back in his chair. “I want you screaming my name until you’re hoarse, sweetheart. Wanna hear you need me.” Dean’s gaze bored into Castiel’s, spreading a heat through his cheeks. The laser focus that Dean provided made him feel trapped, like Dean could see through him. 

He could picture it. Himself, spread out over a bed similar to the huge white one in his room, his ankles and wrists tied down, unable to move. But he didn't feel unsafe in this scenario. Dean leaned over him, kissing him, touching him… 

Castiel wasn't sure why he was trusting Dean with this so soon. He barely knew the man and he had already let Dean suck him down and rut against him until he came spectacularly. And here he was, seriously considering entering a regular sexual relationship with him. 

He saw a flash of a pretty female face with wispy brown hair behind his eyelids, and he felt all the air leave the room.  
Castiel stood, sending Dean back a few paces and knocking the chair back with his momentum. Dean watched him, warily, like he knew he pushed too far. 

“I have to go.” 

Dean gazed at him silently for a moment before he nodded, his face set. “Wasn’t sure how much you were gonna let me get away with, honestly.” 

Castiel started towards the door. Dean made no motion to stop him. He stopped in the doorway and looked back. Dean stayed perched on his desk, eyes tracking across Castiel’s face with a sad hint of a smile playing across his features. 

“I just need time to process this.” Castiel said quietly. 

Dean shrugged. “I get it. This isn’t something you should sign up for on a whim. Just know that if you think about it and agree to come back, we’ll work something out. You deserve to go to school and be what you wanna be, Cas. You shouldn't let them take that from you.”

Castiel felt helpless. “Why me?” 

Dean stood, hands out of his pockets and palm up. “I like you, Cas. You’ve got a lot of light in you, and I dig that. I don't have a whole lot else I’d rather be doing.” He pushed away from the desk and slowly approached Castiel in the doorway. He reached out and pushed a strand of hair away from Castiel’s forehead and pressed a kiss there. 

“Can I give you my number to call if you change your mind or want to talk about things?” Dean’s eyes searched his face, and it occurred to Castiel that perhaps Dean thought he might never see him again. If he wanted to, Castiel could walk out of here and put the entire bizarre encounter behind him like it had never happened and try to work out another way to pay for school… or get back out there and hit the pavement. 

But that also hurt. He didn't want to forget Dean. He didn't know the man very well, but he wanted to. Castiel genuinely liked him already, crazy at it seemed. Dean was kind to strangers, and well-loved by his small family. He was patient and understanding, funny and clever. And devastatingly attractive. 

Castiel needed space to think, but he nodded. Dean just looked at him for a moment, taking in his features, before leaning back to grab another one of his endless sticky notes. He scribbled a number on it and handed it to Castiel. 

“I’m not going to put your number in my phone, because I want you to have the choice to start this. No pressure from me at all, it’s entirely up to you. Call me if you need anything. Please.” 

With that, Dean walked down the hallway without looking back, leaving Castiel standing in the doorway of a rarely used office in a multi-billion dollar home with the number of said multi-billionaire on a yellow sticky note. 

…

Castiel had refused to take Missouri’s offer of hotel fare or even cab fare, instead asking if someone could just please open that huge goddamn gate so he could walk. He needed the space to think. 

It was a pleasant day, the sky a merry blue with only a few clouds in the way. The Pier looked busy from over here, with the Ferris wheel turning and boats zipping around. As Castiel approached the main road, the sounds of the city stood out to him more clearly. A street performer a few blocks down was doing a great cover of whatever Top 40s crap was constantly on the radio of the clubs and bars that Castiel frequented. 

The city was beautiful during the day. Poems and songs were written about the city at night, about its lights and the atmosphere of anticipation. News stations warned about the dangers of the darkest streets, how easily someone unfamiliar to the area could be overpowered. During the day, though, the city belonged to the walkers. The casual passerby dictated the flow of traffic, determined how the buses and trains moved people from place to place. As Castiel joined the crowd headed west, he felt himself relax for the first time since he left. Here in the air, smoggy as it was, he felt better. There was more space here that wasn’t invaded by Dean’s scent and voice and eyes and… 

Right.

Castiel shoved his hands in his pockets. His fingers came into contact with the sticky note he couldn’t quite forget about. He pulled it out and smoothed the creases. Dean’s handwriting was blocky, and he wrote in all capitals, like it wasn’t something he did very often. Castiel wondered how many other guys across the city had this exact number programmed into their phones, or stashed away at the back of a drawer, or tattooed on their memories. Castiel pulled out his phone as well. When it wouldn't light up, he remembered he hadn't had it on since last night, meaning he still hadn't answered Anna’s probable message of panic and worry. 

He looked around and ducked into the nearest Starbucks. The place was reasonably empty for being four in the afternoon. He settled at a table just as he turned his phone on. He set it in the center of the table, and just waited… 

buZZBUZZBUZZBUZZBUZZBUZZBUZZBUZZBUZZBUZZ—

Castiel rolled his eyes as Anna’s name took over his entire lock screen. He smiled apologetically at a nearby patron who was staring at Castiel’s table with mild alarm. 

He sat back and twiddled his thumbs, nodding occasionally when the added Ding! of a voicemail popped up as well. Castiel had expected a hurricane, but this was a goddamn apocalypse. He couldn't blame Anna for being worried, but he could blame her for draining his battery. 

When his phone was caught up, he sighed and unlocked his phone. Seventeen voicemails and forty-six unread messages. Color Castiel impressed. He propped his head up on his hand and scrolled through the messages. 

_Where are you exactly?_

_Castiel you have to have an address???_

_Will you call me at least?_

_Its been four hours, surely you’re done banging him now_

_CALL ME_

_CASTIEL_

_Fine i’ll call you_

_IS YOUR PHONE OFF_

The messages continued like this for thirty-eight more texts, each with increasing amounts of exclamation marks and decreasing amounts of rationality. He punched in Anna’s number, and waited.

“Castiel! Oh thank god, I thought for sure you’d be in a dumpster by now—“

“Anna, I’m fine. And I got all five hundred of your mess—“

“Oh, did you read those? Finally, I was sooooo worried I might have inconvenienced you by trying to figure out where the hell you were—“ Castiel pulled the phone away from his ear when a girl in a green apron approached him with trepidation. 

“Sir, I’m so sorry, but we have a policy that anyone sitting in the restaurant has to buy something…” she glanced at the phone, “unless you’re meeting someone here…?” 

Castiel got up and headed to the counter, apologizing to the girl. While waiting in line, he listens to a bit more of Anna’s very one-sided conversation. One of the best and worst things about Anna is that once she really got going on a topic, she rarely needed an audience. 

“—most bone-headed, STUPIDEST, self-centered move, and you STILL didn’t start the dishwasher! Of course, that’s not why I’m mad, but that’s damn well part of—!” Castiel broke away to order a tall green tea with lemon, handing over the twenty dollar bill still in his pocket. The cashier laughed nervously as he gestured to his phone with a “what can you do” expression and handed him the paper cup. He took his seat again and set the phone down while he opened the lid and stirred in the honey stick that came alongside his cup. 

“—you could have died for god's sake!” Castiel nodded sagely, still just listening to Anna’s tinny voice carry from the phone’s place on the table, “—at least a phone call?” It seemed like she had lost steam for now. Castiel picked up the phone again. 

“I am sorry,” he said. “I just needed some time to think. You won’t believe who I met.” 

Castiel heard her take a breath and hoped she wasn’t gearing up for another screaming match. His phone was on 17% after all. 

“Where did you go? You were going to that bar down South, did you meet up with that guy from the site?” 

Oh, right. Balthazar. “No… there was someone else. Anna, he’s—he’s great. He’s funny and charming, and he’s got these green eyes that—“ 

“Sounds like a crush more than a mark.” Castiel could hear the smile in her voice. Even when she was pissed, she could hassle him. 

“It’s different, Anna. He wants me to—“ Castiel glanced around and dropped his voice, “He wants to pay me to sleep with him. Like as an arrangement.” 

“What, like he’s your sugar daddy or something?” Anna giggles, but stops as soon as she realizes that Castiel isn’t joking. “Jesus, Castiel, how old is he? Is it— you know, is it worth it?” 

Castiel ran a hand through his hair. “That’s what I'm trying to figure out, I guess.” 

“Are you at his house now?” Anna asked, her voice sounded strange. 

“No, I— uh, stepped out for a minute. Wanted some tea.”

“He doesn’t have you trapped there, does he? Like some kept boy? You’re gonna come home eventually, aren't you?” How am I going to pay the rent by myself? she’s really asking. Castiel hadn't thought that part through yet. He couldn't leave Anna. 

“I’ll come home,” he said, and he meant it. He just didn’t know when. 

…

Castiel looked at the post-it the entire train ride to Lake. He looked at it the entire time he was waiting for a bus, and for the entirety of the bus ride. When he got off at Millennium Park, the note was still clutched in his hand, slightly damp now in the summer heat. He sidestepped a loud family with Southern accents making goofy faces in front of Cloudgate, and headed towards the amphitheater. The speakers rained down an album by a local indie band over the crowd milling around. Castiel took a seat on one of the benches facing the theater. He pulled out his phone again and pulled up a new text message. 

_ << Sent:  
Dean? This is Castiel. _

He hit send before he could really think about it. Dean responded sooner than Castiel expected. 

_ >> Incoming:  
Hey Cas, glad to hear from you. _

Nothing else. Dean really wasn’t going to pressure Castiel into this. Castiel leaned back and looked up at the trees. He waited a full minute before returning to the chat window.

_Me: Can I ask a personal question?_

_DW: Shoot._

_Me: Why do you like to tie people up?_

_DW: Damn Cas no beating around the bush?_

_Me: I’ve been wondering_

_DW: I like to be tied because it makes me feel safe. I can't go anywhere but where the one doing the tying wants me to go, and its nice to relax. I like to tie people up to give them that._

_Me: Oh._

_DW: Were you thinking about it?_

Castiel stifled a laugh with a cough. Trust Dean to make him blush even across the city. 

_Me: Yes._

_DW: What were you thinking about?_

_Me: I was thinking about what it would feel like to be tied to your bed._

_DW: Is that something you think you’d like?_

_Me: Is it bad that I don't know?_

_DW: No. More fun for me to try to guess._

_Me: I want to like it. If it’s something you enjoy, it can’t be too bad._

_DW: You’re still not sure about the whole breath play thing, so I dunno if you should use my preferences as a measuring stick._

_Me: I said it was good._

_DW: Can’t fool me, kid. The panic in your eyes was something to behold._

Castiel huffed, and shook his head. An older man that had just sat down next to him was trying to peer over Castiel’s arm to read the conversation on his phone. He raised an eyebrow at the man and tilted the phone away. 

_Me: You just took me by surprise is all_

_DW: Best to get that out of your system early then._

_Me: You wouldn’t choke me if I asked?_

_DW: If you asked for it, maybe. That’s a different situation and something we would discuss beforehand._

_Me: You’re really into talking everything out._

_DW: It’s an important part of this type of relationship, Cas. Consent is the backbone of BDSM._

_Me: I always thought BDSM was more leather and whips than tying someone to your bed and wringing orgasms from them._

_DW: It comes in many forms._

He put down the phone again. He felt seriously out of his element. Castiel wasn’t sure if this whole arrangement was starting to make sense now that he was out in the air with the (relatively) normal people who didn’t whore around Chicago. As he closed his eyes and leaned his head back, a slight breeze picked up, ruffling his hair. 

Why wasn’t there more advice books for people in his situation? 

…

“Castiel, are you sure you’re okay? You were off when you got home and now you’re going out again?” Anna clung to his arm on the platform, almost trying to keep him from getting on the train. 

Castiel gently tugged his sleeve away, not unkindly. “I need to get my head back in order. This’ll be an easy night. I’ve been to this bar before. I’ll be safe.”

Anna’s big blue eyes narrowed in suspicion. “You’re going back to him, aren’t you?”

“N-no, not tonight. I just… need this. For myself.” 

She sighed. “I just want you to know how much I think this is a bad idea, for the record.”

“I know.” 

“But I also want you to know that if you get stuck, you can call me. I’ll come get you, no questions asked.”

Castiel said nothing.

“Okay, I’ll have a few questions, but standard ones. Like ‘what the fuck were you thinking’. But I’ll still come get you.” 

He smiled and hugged her. “I’ll call if I need you—but don’t panic if I don’t come home tonight. I’ll text you, either way.” 

Anna used her position in his arms to smack him on the back of the head, but her face was less drawn than it was earlier. 

Castiel pulled away as the train came screeching to a stop in front of them, the doors opening to reveal a line of tired-looking people sloughing out of the car. When Castiel boarded and took a seat, he waved to Anna as she mimed calling on a telephone at him. He rolled his eyes but nodded. For someone who regularly danced around with tassels covering her nipples, Anna had a lot of maternal instincts just ripping at the seams. 

The ride to the south side was unusually quiet for seven at night. Castiel didn’t remember much of it. He sat in his seat staring straight ahead, and only moved when his stop was called. He shuffled off and down the stairs of the station with the same automaticity. 

He only had one hangup in his line of work, and it was time to lose it. He wasn’t off his game, he wasn’t going soft. 

This was it. 

…

At the end of it, it wouldn't have mattered what the guy looked like, or who he was. The only requirements Castiel had for tonight were: available, interested, and interested in a one-off. He just needed to get this over with so he could lose that pit in his stomach whenever he thought about how inexperienced he still was compared to Dean. 

How much Dean must think he was a child, needing his help. The poor virgin kid out on the streets, trying to make a quick buck. 

No, if he was going to earn this—this seemingly heaven-sent arrangement—he wasn’t about to screw it all up because he had no idea what he was doing. He couldn’t afford to. Not when tuition was on the line, and bills were due in two months. 

The numbers ran through Castiel’s head until a man who clearly met all Castiel’s requirements slid into the seat next to him, hurriedly tucking a small object—wedding ring, Castiel’s experience told him—into his back pocket. Sandy hair, with deep-set laugh lines, this man looked like he just got off at the local Radio Shack. A completely normal, forgettable face. Perfect. 

“How's it going, man?” The man had an casual ease to his voice that made Castiel feel this would be an easy mark. He smiled slowly and really dragged out his response to watch the man’s pupils dilate.

“I was wondering how my evening might end, but I think the answer is in front of me.” Castiel knew he was laying it on thick, but he needed to get this show on the road. He had his ass-virginity to lose. 

The man flushed and grinned crookedly. Easy, easy mark. 

This was the part of his job that made Castiel feel like he was going to make it. When the men were this cavalier, and this engaged, all Castiel had to do was sit back, let their fantasies get the best of them, and watch out for the moment to suggest getting out of this joint already. He wasn’t sure what the man’s name was, but all he cared about were the way he kept reaching back for his wallet, and the shade of green of his eyes. 

The man’s voice dropped down to a whisper, forcing Castiel to lean in. “So… what are you into? You wanna… get out of here?” 

“What do you want me to be into?” Castiel watched the man’s tongue flick out to wet his lips, without feeling any real heat behind the action. Since his experience with Dean, he was beginning to notice exactly where actual attraction fit into his job… and the many places it did not. 

“Will you—“ The man looked around, “Will you let me fuck you in the bathroom?” Even as he said it, his cheeks flushed a darker shade of red. Castiel felt his grin widen even more, feeling like he must look like a viper, knowing he was about to win. 

“Meet you there in fifteen?” The man nodded, and got up, staggering towards the bathroom. Castiel rolled his eyes and finished his club soda. The poor man was probably in there looking himself in the mirror, pumping himself up for what was clearly one of his first experiences in his extra-marital gay experiment. 

Except this time, Castiel actually was taking a dick. 

He took a deep breath. This was just another encounter. Just had to bite the bullet and take it, to get it over with. He didn’t even have to like it, as long as the experience was there. Maybe then he could text Dean and tell him he was ready to make a deal, and properly earn it this time. 

The longer he sat, the more his palms started to sweat. The more his ears started to ring. Castiel shook his head, trying to clear it. He couldn't treat this like a big deal, because it wasn’t. Lots of people had their first time in the bathroom of a skeevy bar; why should this be any different? He didn’t know this man, there was no way he could screw this up. He wouldn't have to face him afterwards, wouldn't have to see the disapproval on his face if he wasn’t up to expectations. Castiel wouldn't have to humiliate himself with his inexperience. 

Castiel’s fifteen minutes were up. He stood up and made his way to the men’s room at the back of the bar. He could feel his vision tunneling, but pushed on. This was how to make everything all better. He watched his hand push the door open and felt his feet carry him into the room. The man stood near the sink, his face breaking into a smile, before schooling it into something more casual and aloof. 

Castiel dropped to his knees, seeking out comfort in the familiar. This would be the easy part. He smirked as he watched the man’s eyes widen almost comically as he slowly drew the man’s zipper down, reaching inside to pull out his already stiff cock.

These closet-cases always got it up so fast, it almost wasn’t even fun. 

He let himself sink into his “client” mind space as he worked the man’s cock over, paying attention to when his breath went ragged, and when he swore, wiping sweat away from his brow. 

Too soon, Castiel was being hauled up and propped up on the sink, the man almost tearing at his pants button in his inexperienced urgency to get at skin. 

“Can I—I know I asked… can I actually f-fuck you?” He asked shakily, his hands skidding everywhere over Castiel’s still-clothed body. Castiel felt feverish, but he wasn’t a hundred percent sure it was from the heat of the moment. 

“Y-yes.” He said it. He wasn't going to take it back. The man tried to kiss him, but Castiel leaned away, distracting the man from his disappointment by sucking a vicious hickey under his left ear. Let his wife at home find that the next morning. “Do you have lube?”

The man fumbled in his pocket and produced a packet of generic lube that definitely came out of the vending machine bolted crookedly to the right of the door. “I know what to do.” He seemed trying to convince himself, as well as Castiel. 

Castiel allowed his pants to be slid over his knees, and himself to be leaned back. As he spread his knees, allowing access to the place on him that had the man’s breath catching in his throat, he wondered if this would be Dean’s reaction as well. Would he treat it like a gift, or like something that was expected? 

The man fumbled a bit of lube onto his finger, before jabbing it at Castiel’s hole. He gasped and tried to settle back. While there was some knowledge there, the man’s expression couldn’t have been more stressed. He constantly kept darting between where his finger was playing a staccato rhythm and Castiel’s face, as if to make sure he was doing alright. 

This wasn't working. He couldn't do this. The room’s fluorescent lights buzzed all the louder in Castiel’s ear, and combined with the hum from the bar beyond the door that Castiel could still here. Was the door even locked? What if someone came in? Was this man even clean? Were they going to use a condom? The jabbing at his hole suddenly felt eleven times more uncomfortable as the feelings mounted like a wave, high above Castiel’s head. It wasn't like this with Dean, this was bad. 

It was too much, too much, _too much._

“Stop! Please!” He squirmed away and the man leaped away from him as if he’d been burned. 

“I’m sorry! I’m sorry! It—I didn’t…” The man crowded himself along the opposite wall, trying to give Castiel as much room as he could in the small space. Castiel tucked himself back in his pants and pulled the rest of his body onto the counter. He took a deep breath. 

“No, I just—thank you… for stopping.” 

“This isn’t gonna work, is it?” The man looked… sad. Castiel felt a rush of guilt, but pushed it down. He wouldn't make it through this encounter if they took it all the way. He shook his head in response. 

The man shrugged and looked down, hoisting his pants back up and fastening his belt. “S’pose that’s what I get, honestly,” he looked up at Castiel. “I’m married, y’know? Shayla and I have been together for seven years, this November.” 

“Does she know why you’re here?” Castiel asked, honestly curious. 

The man shook his head. “I don’t even really know why I’m here either. Thought it might help clear up… everything, but I don’t know. I don’t think I’m gay… but how do you know?” The man looked up at him with such a lost expression, that Castiel couldn't help but feel bad for him. “How do you know you want the person that you think you want?” 

Castiel blinked about a dozen times and once more for good measure and shrugged. The man sighed and trudged out of the bathroom, a heavy set to his shoulders. Castiel scrambled off the counter and adjusted his clothing. He swung around to face the mirror, and scrubbed his hands through his hair. He pulled out his phone and dialed the number he had memorized, simply by staring at the page on which the number was written all damn day. 

The person on the other side picked up after the first ring.

“Cas! To what do I owe the pleasure of a phone call?” His voice sounded cheerful and relaxed, so opposite the way Castiel felt in that moment. 

“Dean, I want to make a contract.”

**Notes for the Chapter:**

> Rofl, please note that not only was I writing a sex scene, but it was a BAD sex scene. Bless up, y'all. We'll get to some good stuff later.


	5. Ultraviolet

**Summary for the Chapter:**

> Decisions are made, and consequences are realized.

**Notes for the Chapter:**

> Hey folks! Sorry this wasn't up earlier; I recently had a parent get hospitalized, so this had to get pushed back a bit. Thankfully, it's only a day late! 
> 
> Tell your friends and leave a comment if you like this story! I'd love to hear your feedback!
> 
> -azo

Silence met him on the other line, making the back of Castiel’s neck start to sweat and his stomach to swoop. Was he wrong? Did Dean not want this anymore?

“You wanna run that by me one more time?” Dean spoke like he was trying to avoid spooking a horse or a mental patient, “Are you okay?” 

“I want to make a deal. For real this time,” Castiel said this very fast, trying to get the words out. “No backing out, no more waiting. I’m ready.” 

The next time Dean spoke, it was in a strange tone. Gone was the lighthearted teasing and slight confusion. Dean was all business now, but his business sounded slick and inviting. “Can I come get you and bring you back to my place?” 

Castiel was confused. “I—yes, but Dean. I’m really ready. I want this. Right now.” 

“You said that already, sweetheart,” Castiel’s insides jumped at the way Dean’s voice curved over the pet name, “but there’s a lot we gotta discuss first. Tell me where you are and I’ll come get you.” 

Castiel stepped out of the restroom, phone still pressed to his ear. The rest of the bar seemed obnoxiously loud and bright. He ignored the knowing glance of the bartender, who had no doubt seen everything, and walked right out the front doors into the dark of the night. He told Dean the name of the bar and heard a snort on the other side of the phone. 

“Geez, that's a dive for sure. You makin’ a habit of this, Cas? Hangin’ out in skeevy bars with sleazebags?” 

“It’s how I met you, isn't it? Please hurry.” 

“I’m on my way.” The line clicked and Castiel was left with the sodium flare yellow of the street light washing out his skin and the bustle of the bar behind him. 

Castiel moved out of the way of a very drunk couple coming out of the bar, and moved to the corner, right beneath the street light, next to an empty newspaper stand with the hinged door swaying open in the slight breeze. He hadn’t smoked in months, but the atmosphere made him need a cigarette, if not just for something to do. 

Dean was coming for him. He was going to make a deal with Dean and sleep with him for money. It shouldn't have been this hard to deliberate his choice, he sucked cock in alleys of bars similar to this on the regular. He was looking for a catch, but he hadn’t found one yet. And the contract. The contract wouldn’t necessarily keep him safe, it wasn’t like he could go to the police if his john went back on his terms. But having a set list of rules would be comforting. As long as he kept his wits about him, he could come out of this on top.

No pun intended. 

The doors to the bar opened again, and a crowd of men talking loudly exited. The tallest of the group was wearing a short sleeve button up that looked two sizes two small, and about three years past the date it should have been tossed. He threw his head back and laughed, while punching a shorter man’s arm. The shorter man looked distinctly uncomfortable and shoved his hands in his pockets. When he looked up, Castiel noticed he was the same man who had had his finger up his asshole not fifteen minutes ago. The man glanced around and saw him standing there, no doubt looking like he was trying to get away. From his place thirty feet away, Castiel could see the man’s face turn a ghostly white, and then blushing crimson. One of his companions slapped him on the back and asked him if he’d seen a ghost. He jumped and resolute turned away from Castiel, walking the opposite way. His group of friends laughed and ran to catch up with him, none the wiser. 

Castiel smiled and shook his head. The closet cases were always a bit of fun, if in a sad way. People so out of touch with their own wants that they treated encounters with people of the same gender as something to be ashamed of, hidden. It really _did_ something for the client if they thought what they were doing was taboo. People who knew what they wanted, knew how to ask for it though, however few and far between, they made Castiel forget what he was doing was supposed to be shameful. 

A familiar black car pulled up to the curb and the darkened window rolled down.

“Dean.” Castiel breathed out in relief. 

Though Castiel had seen the same smile cross Dean’s face at least a dozen times in the past twenty-four hours, it still radiated light in the dark. Sometimes, the hardest part of Castiel’s job was pretending there was attraction between him and the john, or real reason behind the sex that wasn’t money. It would clearly be no problem with Dean. Dean licked his lips, “Heya Cas. Come for a ride with me?” 

Castiel didn’t worry about looking too eager, glad to get away from the bar. He pulled open the car door and scrambled in as fast as he could. “Thanks for coming to get me.” 

Dean pulled the car away from the curb and turned a corner to head east. “No problem. Nobody was giving you trouble, were they?”

Now that he was in the car and closer to the smell of Dean’s cologne and the sight of his strong hands on the steering wheel, Castiel could feel it. He wasn’t quite sure what “it” was yet, be it attraction or something else, but there was something so magnetic about the man in front of him that he couldn't wait to get started. “No, they weren’t—“ He leaned over and put his hand on Dean’s knee, brushing upwards to get to his crotch. He’d seen Dean’s cock once before, but suddenly it wasn’t enough. Dean’s fingers curled around his and stopped his motion, holding his hand now. His thumb stroked over Castiel’s hand. It felt nice, but it wasn’t what he wanted. 

“—Dean, I want to sub for you. Please, let me—“ 

“We’ll discuss that after we get you something to eat, and maybe after you tell me a little bit of what’s going on.” Dean’s tone was firm. 

Castiel tilted his head. Maybe Dean had changed his mind? “You don’t... You don’t want me to do it anymore? I thought—“ 

“You know that’s not it, Cas—“

“Then why won’t you…? Is it because you’re driving? Pull over and—“ 

“No.” Dean tore his eyes away from the road to emphasize with his eyes. 

Castiel pulled his hand back. “Did I do something wrong?” 

Dean sighed. “Cas, yesterday you hightailed it out of my pace as fast as you could. Don't blame me for having a couple questions as to why you’re so gung-ho now.”

“I just— “ 

“Later Castiel.” Dean’s tone was sharper now, leaving no room for argument. It was one of the only times he had ever used Castiel’s full name and he didn’t like the sound of it in Dean’s mouth. 

Castiel snapped his jaw shut and settled back against the seat, leaving silence in the darkened car. 

…

It was a different diner this time; in a different part of the city. This diner clearly catered toward a younger clientele, as there were things like “avocado toast” and “croissant grilled cheese” on the menu. Castiel kept his mouth shut the entire time Dean was leading him into a booth and conceded to let Dean order for him as well. If he was going to keep his dom—sugar daddy—whatever he had going, he was going to cling to it by the skin of his teeth and be good. 

Dean carefully kept his eyes wandering around the restaurant and didn’t fixate on Castiel for too long. Castiel didn’t take it as a very good sign, and tried to keep his features looking pleasant, and not pouty, even though all he wanted was to grab Dean by his too-straight collar and demand to be taken right there. 

The sign for the attorney’s office across the street was flickering, the letters doing their best impression of a strobe light on depressants. The pink hue of the light caught at Dean’s face and made the green of his eyes electrify into a more radioactive shade. To keep himself occupied, Castiel mentally toyed with the shades he’d use to get the color right. 

Cadmium yellow was a must. Maybe a bit of ultramarine with some cerulean. Old painting masters would preach about the simplicity of using alizarin crimson, ultramarine, and ochre to achieve any color palette you would need, but the fact of the matter was that most of those shades were too dull to do much of anything besides landscapes of European countrysides. Real life was much more colorful and vibrant than what the refined but tired traditional paints could give. But Castiel always kept a tube or three of ultramarine blue around. Just a dot could give immeasurable depth to indigos and greens.

Greens were the hardest to get right. Too much yellow, and you wound up in chartreuse territory, with a predilection towards olive. Too much blue, and you were stuck in aqua and turquoise, with no way out. Castiel thought that emerald would be too extreme for Dean's particular shade. Maybe more of a candy apple or Granny Smith. 

“Here ya go, gentlemen.” A server dropped off two plates and popped her gum twice before leaving again. Castiel had no idea what had been ordered for him, but appreciated that Dean got French toast for him. Something simple and comforting. Feeling ravenous, he dug into his food, watching Dean do the same, but slightly messier. Castiel smirked around his fork when a bit of syrup landed on Dean’s leather jacket sleeve. 

Castiel wondered if Dean was purposefully keeping him waiting, or if he was seeing how long it would take Castiel to push him into talking. Castiel wasn’t sure what the right answer was. 

Finally, Dean wiped off his mouth and sat back, looking right at Castiel for the first time since they had sat down. “I’m really torn between going back to the privacy of my place, or keeping you in public where there’s witnesses.” 

Castiel raised an eyebrow and licked his lips, “Are we going to need witnesses?” 

“I’m not sure. I just don't know if I should be alone with you like this.”

“Like what?” Castiel huffed. “I’m fine. I told you, I want to make a deal with y—“ He fell silent when Dean raised a hand. 

“Alright, my place it is. If that’s okay with you? It’s your choice of course.” Castiel nodded furiously. “Let’s roll, Kato.” 

Castiel frowned. “I-it’s Castiel…?” 

“No—Kato was the sidekick for… for the Green Hornet—okay, never mind. Let’s just go.” Dean flushed slightly, throwing a few bills on the table and ushering him out the door and back into the car. 

Back in the darkness of Dean’s car, which Castiel noted was an Impala by the shiny silver script on the tail, he inched his hand over by Dean’s again, hoping against hope that Dean wouldn’t push him away if he made it clear he wasn’t trying to cause trouble. He wanted to feel connected to the man by skin again, even if it was just by meager hand contact. He didn’t dare look, but breathed out a sigh of relief when Dean’s warm fingers wove between his. He let the lightness of the contact fill him up and carry him out of the car when it stopped in front of Dean’s enormous castle of a house, through the dignified living room, and into the hallway outside of the study. Dean opened the door and Castiel caught his wary gaze, wondering if Castiel would walk out again, this time for good. 

Castiel settled into the plush chair, still in the same position from the last time he was here in this room. Dean leaned against the edge of his desk, shrugging off his jacket, and folding his henley-covered arms. Here, he looked about ten years older than he usually did. 

“So,” he started, looking Castiel up and down in a way that made him feel the need to hide and preen simultaneously, “Something happened between yesterday afternoon and an hour and a half ago that made you change your mind on the whole sub thing. You wanna tell me about it or should I guess?” 

Castiel worked his jaw for a moment. “I want you. You’d be good to me, I can feel—“ Dean made a face and cut him off with a wave. 

“Don’t tell me what you think I wanna hear. If you’re not gonna be honest with me, I’m not interested.” 

He hesitated. “I still need the money. I want to go to school.” 

“And you think selling yourself is the way to do it?” Dean used no inflection, no emotion. 

Castiel balked. “When you put it like that, it sounds… dirty.” He had no illusions as to the perceived morality of what he did, but usually the buyer of his services didn’t make it sound so blunt. 

“Cas, I’m paying for the chance to sleep with you and boss you around. I dunno how you want me to phrase it.” 

“Yes, I think the present opportunity would be the most efficient means of getting enough money by September 1st.” 

Dean clapped his hands on his knees and straightened up. “Then let’s make a deal.” 

…

At the end of the day, let it be known that Castiel James Novak tried for twenty minutes to get Dean Samuel Winchester of Winchester Holdings, LLC. to agree to the promise of one (1) extravagant gift a month, but was overruled by the presenting party, who countered with the potential for four (4) eixtravegnet gifts per week. 

“That’s practically one every other day!” Castiel couldn’t fathom the amount of money Dean was willing to spend on him. 

Dean smiled crookedly. “Don’t sass me, or I’ll up it to every single day!” he crowed. 

“What do you consider an ‘extravagant’ gift?” Castiel asked. 

The billionaire shrugged. “Could be anything. Top of the line paints, a new suit… a car.” 

Castiel’s eyes widened almost comically. “A car—! No no no no no, I can’t accept a car. I don’t even have a place to park it at my shitty apartment.” 

“That reminds me,” Dean plucked the pen from behind his ear again and jotted something down. “You got a roommate, yeah? Where do you think she’d want to live?” 

“What?”

“You think she’d like Hyde Park or Lakeview better?” 

Castiel gaped at him. Hyde Park was one of the most sought after neighborhoods in the entire city. Castiel would have killed to get clients who even frequented the area, let alone lived there. Dean smiled serenely back at him. 

“Gotta keep you safe, sweetheart. After you sign this… you are my property,” Dean looked up at him from under his lashes, smirking. “Sort of, anyway.” He chuckled like he was making a joke to himself. 

The rest of the contract wound up detailing all the different ways Dean was allowed to spoil Castiel, as well as the hard limits that the both of them had. On the list of accepted acts was: dirty talk, blowjobs (giving and receiving), vibrators, breathplay (Dean huffed as he wrote this down), and bondage (with a dark and imposing question mark next to it, as Castiel had yet to see it in action yet) among other things.

“And remember, any time you feel even the slightest bit uncomfortable with what we’re doing, you have to tell me. I won’t sign unless you promise to keep me in the loop, okay?” Castiel nodded and reached for the pen. Dean pulled it away and got right in his face, “Promise me, Castiel. Make sure you mean it.” 

Castiel held his hand out like a Boy Scout, which was the most ironic thing, maybe in the history of the world, “I promise, Dean. Honest.” 

Dean held his gaze for a moment longer, before handing the paper over, along with a pen. Once both of their signatures were on it, Dean rolled up the contract and tucked it in a drawer of the desk. 

“I know it’s not really legally binding, but I’m gonna have my brother look over it to make sure it’s all kosher… ya know, to make me feel better about being such a skeeze.” 

Castiel raised an eyebrow. “Your brother?” 

Dean grinned. “Sammy-boy’s a lawyer and everything. Won’t shut up about it.” Dean’s expression told Castiel that maybe it wasn't Sam that bragged about it to everyone.

Castiel looked around, maybe expecting something to feel different now that he was now a contracted whore for one of the richest men in the city. Mostly, he just felt warm. The house was a comfortable temperature, but the dark paneled wood and the yellow lighting was making him feel a few degrees higher than normal. 

Of course, it also could have had something to do with the man whose gaze was boring white-hot holes into him. 

Dean tilted his head and let a smile spread across his face and he slowly looked Castiel up and down. 

“Are you… happy with this arrangement?” Castiel had to ask. 

Dean nodded and the crinkles around his eyes deepened a bit. Still he did not speak. 

“Is there something you want me to be doing right now…? Do you want a drink?” Castiel fidgeted with his belt loop. All this not-talking-or-getting-down-to-business was making him feel antsy and out of his element. 

Dean shook his head and stalked forward, placing his hands on the armrests of Castiel’s chair, much like how they had been the previous day. Again, Castiel backup up, pressing himself into the fabric of the chair. He looked up into Dean’s green eyes and felt all the breath leave his body. Dean’s face was coming closer and closer to his, shrinking the space between their lips and Castiel was ready—Dear god, he was so ready to have this again…

… but he didn’t get it. Dean changed course to put his lips by Castiel’s ear. When he spoke, his lips brushed Castiel’s lobe, making him shiver. “I’m going to watch the news in my room, and I’d like you to join me.”

Dean retreated, leaving Castiel’s chest heaving, but nodding all the same. Dean strode out of the room, graceful as ever, with Castiel hot on his heels, if a little shaky. 

They passed the room Castiel had stayed in the previous night, and headed straight for the double doors at the end. Castiel was excited to see where Dean slept every night. Was he messy? An obsessive neat freak like the rest of the house suggested? Was there anything embarrassing? 

Dean pushed open the heavy doors and crossed the threshold, because to him, this was just his room. It wasn’t a peek into the world of someone he barely knew but desperately wanted to. A giant white and unmade bed sat in the center, underneath a domed skylight set deep into the high ceiling. A sitting area crowded rather cosily around a flat screen television that almost matched its twin in the living room. Like Castiel’s room had featured, the far wall was entirely glass, letting out onto a private patio area with a clear view of a dock out on the lake. To Castiel’s amusement, the end of the dock housed a green light, blinking benignly. 

Castiel hoped he’d be spending a lot of time in this room. And maybe if the en-suite bathroom he could see beyond a propped open door had a bathtub, in there as well. 

Dean pulled off his shirt and whipped it towards the closet, uncaring of where it landed. Castiel had to control himself from sucking in a breath at the sight of his skin. He turned and smirked at Castiel as he was taking down his jeans, which told him that he apparently wasn’t doing a fantastic job of keeping his cool. The man sidled up next to him in only his black boxer-briefs and gripped the hem of his shirt, asking permission with his eyes. When Castiel nodded, the shirt came off, as well as his pants were pushed down, leaving him standing in the expansive room in tented boxers and a wide-eyed expression. 

With a chuckle, Dean leaned in again. “Stop looking at me like that, man. You’re the prize here, not me.” He grabbed Castiel’s hand and towed him towards the sitting area. Dean sat down first and pulled Castiel on top of him. But it wasn't right—Castiel was facing the television and Dean shifted him so that he was leaned against Dean’s left arm, not facing him at all. 

Castiel raised an eyebrow as Dean flicked on the television with another one of those tablet-remote things that Castiel hoped no one ever asked him to use. “That’s it? You just want me to sit on your lap?”

“Is that a problem?” Dean asked, grin evident in his voice. 

“No, I just thought there’d be more… I dunno—“

“You thought we’d get down n’ dirty right away?” 

Castiel had done many a depraved thing in his life, but that question made heat crowd up under his jaw and into his cheeks. “Ye-es?” Like it was a question. 

“I want you to feel comfortable asking questions when you don’t understand something. Don’t feel like you can’t ask for something you want. I told you, you’re in control here, really.” Dean went back to watching Leno hassle his guest about something ridiculous they had done over the weekend. 

“Okay.” Castiel wasn’t sure if he was disappointed or not. He tried to settle back into Dean’s warmth. He wanted to focus on the show, because Dean was clearly into it, but instead, he was hyper aware of the feel of Dean’s skin along his bare shoulders. The amount of heat that he put off was astounding on a normal occasion, but surrounded like this, even as casual as it was, made Castiel’s blood run a little bit faster. 

He was also made aware of the tickling sensation along his arm when Dean started stroking gently, seemingly unaware. The motion sent sparks running crazily up his arm, going faster when Dean’s hand moved to his ribs. Castiel held his breath, trying not to laugh, until Dean moved lower to a less ticklish spot. Dean’s fingers massaged lightly over his stomach, and Castiel was suddenly conscious of all the meals he had missed out on over the past few weeks. He was much skinnier than he should be. Dean didn’t seem to mind, or at least didn’t comment on it, just moved lower to toy with the waistband of his boxers. 

Castiel looked over at Dean’s profile, trying to gauge where this was headed. As Dean’s hand slipped down to palm his quickly-filling erection, Castiel gasped, and tried to cover it with a cough as Dean looked over in confusion that Castiel could see through in a second. 

Dean’s hand stroked him, played with his shaft, and ground against the head of his cock, making him squirm. Oh, but this was just like Dean, wasn’t it? Start off innocent, but spiral into something so dirty, you couldn't help but feel like you were getting away with too much. Castiel gasped as his touch increased in pressure, giving him something delightfully firm to grind into, while feeling sweat start pooling at his back. 

Suddenly, Dean leaned in. “You’re gettin’ awfully jumpy over there, Cas. Is there something you want?” 

The heat in Castiel’s stomach was speeding towards his fingertips, making it hard to speak. “I—I want…” 

Dean pressed a kiss behind his ear, “You have to tell me or I’m afraid I can’t help you.” Dean’s voice sounded sad at the end, like he wanted nothing more than to be helpful. The dick. 

“Touch me, Dean.” Castiel ground out. 

Dean pulled his hands away, only to grip Castiel’s arms and swing him around so that he was straddling Dean’s thighs. “Touch you where?” He asked, eyes roaming all over Castiel’s form, from his peaked nipples to where his cock was clearly straining in his underwear. Through his haze, Castiel was delighted to see that Dean was in a similar predicament of his own. Dean ran his hands all over Castiel’s body. He petted his thighs, grazing over the place Castiel needed it most, grinning as he listened to him whimper. Finally, one of his hands alighted on his throbbing cock, making Castiel’s hips thrust in sheer arousal. “Oh, here? You want my hands here?”

“Yes!” Castiel ducked his head to lean against Dean’s muscled shoulder, feeling the sweat of his forehead slip against Dean’s skin but utterly uncaring. 

“But what about here?” Dean grabbed two big handfuls of his ass, using his leverage to grind Castiel forward into his own cock. Castiel keened and blindly bit the skin of Dean’s shoulder. When Dean locked up, Castiel glanced up, terrified he had ruined the moment. Dean’s lust-crazed look met his. 

“Do it again.” 

Dean put his hands on either side of Castiel’s hips and moved him, thrusting into him and rubbing every mind-searingly hot inch of his glorious cock against Castiel’s. “That’s it,” he crowed, kissing Castiel shallowly between words. “That’s it, Cas. Is this doin’ it for you? Got you so hard for me, just like this?” Castiel nodded, not even hearing sentences anymore, but lost in the sweat and feel of Dean’s mouth beneath his. “Such a good boy, bringing so good on my lap.” 

“Dean—! I’m gonna—oh, you’re gonna make me—“ Castiel cried, gasping for breath. He pulled back from Dean’s mouth to pant against his throat, using the opportunity to bite along the thin skin there, press his lips to Dean’s Adam’s Apple. He felt more than heard when Dean’s groan answered his actions. 

“Do it. Please, baby, I want you to.” Dean thrust up once more and lifted Castiel with his hips as his cock spurted inside his boxer-briefs, the wet spot growing rapidly and warm beneath Castiel. It took Castiel only a second longer, before he pressed himself as hard as he could against Dean, humping into him hard and gritting his teeth as he rode it out. 

Castiel huffed as he thumped his head onto Dean’s shoulder. He should probably have asked before getting cuddly, but the way Dean’s hands came up to stroke his sweaty back told him this might just be okay without asking. 

“See, Cas?” Castiel tried to lift his head to look at Dean while he was talking, but couldn't find the energy. “This is what we call ‘foreplay,’ and ain’t it a beautiful thing?” 

Castiel huffed out a laugh. Beautiful, indeed.


	6. That's What You Get For Waking Up in (A Lakeside Mansion)

**Summary for the Chapter:**

> Castiel wakes up, and has some business to attend to.

**Notes for the Chapter:**

> Hello! For those of you keeping score at home, you may notice that I did not post a chapter last week. I do apologize for that. Life has a funny way of getting in the way sometimes. Hopefully, between school, work, and visiting the hospital, I can get back to some sort of schedule, but in the meantime, I can offer you this update. 
> 
> Please enjoy and leave a comment if you like! 
> 
> -azo

When Castiel woke up the next morning, it was to the bright light spilling from the picture window in his own room. That is, the room that was considered his in Dean’s enormous lakeside mansion. Castiel wondered if Dean ever considered how very Batman-esque his abode made him seem. He sat up and stretched, scratching absently at a hickey on his throat. Though the marking of skin was not technically on the “allowed” list of acts between Dean and himself, he couldn't find it within himself to care very much. 

After Dean finished “watching the news” last night, he offered Castiel the choice of sleeping in his own room or with Dean himself. As much as Castiel wanted to be close to Dean, he still couldn't shake the feeling of needing to create distance between himself and his john. He knew that as a sub or a sugar baby, or whatever Castiel’s title was, he should be wanting to spend as much time with Dean as possible…

But months of habit were hard to break in one night. So, Castiel had instead chosen to sleep next door, a decision that was not met with any animosity or disappointment, just a smile, a quick kiss, and a quiet goodnight. In his solitude, Castiel found himself going over the evening, smiling and feeling his cheeks warm, despite himself. 

So here Castiel was, just waking up in the plush spare room of his billionaire client. As he worked himself out of the grogginess of waking, Castiel wondered where Dean was now, if he was at work or if Castiel would find him in the kitchen, making pancakes with Missouri again, chatting like normal family members or roommates—

Shit. Anna. 

Castiel scrambled out of bed and over to where he had dropped off his pile of clothes last night. His phone sat quietly in his pants pocket, right where he had left it… quietly—because it was dead. Castiel brought the phone back over to the unmade bed and dug in the drawers of the modular side table. This man kept a fully stocked bar in all three of his living rooms, surely he would have thought to stock his guest rooms with the same sense of preparedness?

“Oh bless you, Dean.” Castiel said aloud, hurriedly plugging his phone into the wall with one of the three charging cords tucked neatly into the drawer. The phone’s screen glowed almost resentfully as it booted up.

“Not usually the context I hear that in,” a melodic voice caught Castiel’s attention from the doorway. Missouri stood in the doorway, a laundry basket balanced on her hip. 

Castiel looked down, noting that he was still in his boxers. He blushed. “I was just looking for a charger… f-for my phone.” He held up the device, still unsure how he should handle Missouri. 

“Dean mentioned you might need some things washed since you left your things at your place and won’t get a chance to get them until later.” 

“Uh yeah… I need to go grab some clothes, since I might be… staying a while… if that’s okay…?” Castiel had no idea why he was sounding so nervous. 

Missouri’s face broke out into a smile. “Honestly, it’s been so nice to see Dean so happy these past few days. Usually he spends all his time locked down in that garage and I hardly see him, even at meal times.” She started bustling around the room, straightening the sheets and pillows on the bed. 

Castiel looked around, wondering how to help her, but not wanting to awkwardly ask. He settled for straightening the heavy drapes as he gazed out onto the lake. “Does he do his own work on his car?” he asked mostly for conversation, but finding himself genuinely interested as soon as he asked. 

“Oh yes,” Missouri said, snatching up Castiel’s discarded t-shirt and dropping it into her basket. “He’s got about five cars down there that I know he’s working on. The boy comes to breakfast with grease under his fingernails, and bags under his eyes. It’s not healthy.” She replaces his t-shirt with a clean one from out of nowhere. Castiel can’t be sure, but judging from the size, he’s pretty sure it’s one of Dean’s. 

“Do you think that’d be where he is now?” 

Missouri looked up and smiled. “I’d be willing to bet. It’s down the hall and down a flight on stairs on the left. You can always tell what kind of mood he’s in by what volume the music’s at. The more likely you are to lose an eardrum, the better he feels.” She walked into the bathroom to change towels and breezed out the door again. 

“Since you’re going down, I’ll leave you with some breakfast for you, and some to take down to Dean. Lord knows that cars are the only thing that can make that boy forget to eat.” She disappeared down the hall. Castiel hung back only a moment, before realizing he didn’t remember where the kitchen was to get the food Missouri meant him to take to Dean. He stepped out into the hallway, where he saw a covered tray sitting on the little accent table outside of his room. He lifted the lid and saw scrambled eggs, sausage, toast, and juice, two servings of everything. He looked up and where Missouri had disappeared to. 

She had known he’d go find Dean all along. 

…

After descending the stairs, Castiel followed the sound of blaring AC/DC further down the hallway. As he got closer, he heard a man’s voice he thought might be Dean singing—trying to sing along, in a way that was rather off-key. Castiel chuckled as he pushed open the heavy door with his arm that led into an expansive vehicle bay with concrete walls and flooring. 

A pair of denim-encased legs poked out of the bottom of a sleek hot rod red two-seater car that looked straight out of a James Dean movie. The spoiler on the back had a pinstripe design and swirling type that said “Trouble in Paradise” in yellow. Castiel walked closer to the car and as the song changed to something Castiel was reasonably sure was by Led Zeppelin, the same off-key singing sounded again from beneath the undercarriage. Castiel smiled and shook his head, setting down the tray before leaning against a work bench, covered in tools. 

“—well I still don’t seem to caaaaaaaaaare—“ Dean belted as he rolled out from underneath. He stood up and wiggled his hips a bit as if he was performing for an audience. Castiel couldn't hide his laugh. Dean jumped at the sound, which only made Castiel laugh harder. 

“Alright, alright, you come into my house and disrespect me like this…” Dean was beaming through his embarrassed blush. He came closer and tugged Castiel in for a quick kiss. “What’s up, Cas? Sleep well? And do I smell Missouri’s cooking?” 

Castiel nodded. “She sent me down with breakfast. She said that you can forget to eat down here.” 

Dean shrugged. “That woman knows me too well.” He lifted the lid and took a piece of sausage, sticking it in his mouth like a cigar. He reached for a wrench and turned back to the car. “Is that the only reason you came down?” 

Castiel took a breath. “I actually came to see if you’d let me run home for a few hours. I need to drop off a check for Anna, and I wanted to grab a few things. I’ll come right back.” 

Dean chuckled, “You don't gotta ask permission, you know.” 

Castiel shrugged. “Just thought you’d want to know where I am. Unless you want me to do something.” 

Turning and raising an eyebrow, Dean looked him over. “What should I be asking you to do?” 

“I dunno. I can’t really cook or anything, but if you… wanted something.” 

Dean’s mouth curled into a slow smile. “And what could I possibly want, young Castiel?” 

Castiel felt a blush creep up. He grinned. “Beats me. But you know… while I’m here…” 

Dean dropped the rag he was holding on the side of the car, the grease smearing on the shiny red paint. Not that he paid it any mind. “Are you trying to get me into your pants, Cas?” He advanced, backing Castiel up to the gray sectional sofa behind them, attached to a small kitchenette with a fridge and sink. When Castiel’s knees hit the sofa, he sank down, brushing catalogs for car parts out of the way. Dean clambered up with him, knees settling on either side of his lap. 

“You seemed pretty eager to get into my pants yesterday.” Castiel liked how easy it was to tease Dean, and how much Dean seemed to like getting teased. 

Dean’s strong fingers stroked over his hips and got a grip. In a smooth motion, he fell to the side, pulling Castiel on top of him. In two seconds, their positions had been reversed, with Castiel now sitting astride Dean’s lap, breathless again. Dean pulled Castiel in and sealed their mouths together, immediately pushing his tongue into Castiel’s mouth. 

Castiel _loved_ kissing Dean. Sometimes his johns would request it, another piece of the fantasy. They wanted to feel like they were getting away with something that couldn't be bought. They were wrong, anything could be bought, emotion could be faked, hitched breath could be fabricated, but money was always exchanged in the end. And while Castiel was getting paid for this, he couldn't help but feel that he was the one getting away with something. 

Dean kissed like he seemed to live. Brash and unapologetic, but almost unbearably sweet. He knew how to kiss, knew how to make the other person feel it all the way down to their toes, and clearly enjoyed doing it. Castiel pulled back, needing to breathe, but Dean just followed his lips, dragging him in again. Dean kept one hand low on his back, stroking the skin that peeked from between Castiel’s shirt and pants. Castiel couldn't have pulled away first if he wanted to. 

When Dean finally let him surface for air, they were both panting and grinning manically at each other. 

“Was that really why you came down to find me?” Dean winked at him. 

Castiel rubbed his hands across Dean’s chest and down his shoulders to his biceps. “That was a bonus, but I really do need to see Anna, the rent’s due today.” 

Dean patted Castiel’s hip as a gesture to get up, and when Castiel acquiesced, he went over to a metal desk by the rolling work bench. A bunch of papers were setting upon the desk’s surface, and Dean rummaged through them for a bit. He came up with a checkbook and a pen, which he brought back to where Castiel sat on the couch. 

“Who do I make it out to?” 

“Dean, you don’t have to pay my rent too, I still have a check upstairs,” Castiel protested. The first check, which Dean had given him last night before they parted in his room, was for over a thousand dollars for, as Dean put it, “services thus far,” which was said with a saucy wink. Castiel couldn't believe it, and if it weren't for the evidence that the clearly expensive mansion he was currently seated in provided, he might scoff and write the check off as a fake.

Dean blinked and sat down beside Castiel. “Cas, do you remember that contract I had you sign yesterday?”

“Ye-es?” Castiel was confused. 

“Did it say that you could dictate what I paid for, outside of the agreement of your tuition and supplies therein?” 

“Um, no?” Castiel was suddenly aware that he was being led into a trap.

“And do you, Castiel, think that I, Dean, am a competent adult with full capacity to discern what I can and cannot spend my own money on?” 

“Are you sure that Sam’s the lawyer in the family?” 

“Cas—“ 

“Fine. Pay my rent. See if I care…” He took the check that a beaming Dean handed him. He glanced at the amount. “How do you even know how much I pay for rent? This is more than my half, this is both mine and—“ 

“I had to estimate, but it should cover it, right? And hey, when you get back, I have a surprise.” 

Castiel huffed. Anna wouldn't believe this. “Thank you.” He slipped out of his seat on the couch, and sank to his knees in front of Dean, spreading the man’s legs so he had room to sit. Again, Dean blinked. 

“Cas, you don’t have to—“ 

“Isn’t this what I’m here for?” Castiel reached out and palmed Dean’s crotch, pleased when Dean gasped and his cock started filling. He leaned forward, meaning to place his lips on the bulge and draw the zipper down with his teeth, a move that always drove his johns mad. However, before he could, Dean grabbed him under the chin and pulled him up for a kiss. 

They pulled apart. Dean looked rather contrite. “Sorry, it’s just—“ He looked down, green eyes darting around. 

“It’s okay,” Castiel said, grabbing Dean’s hand with his own. When Dean loosened his grip enough, Castiel moved his hand just a bit downwards, right over his throat. “Can we do this for a bit more though? Before I go? I’ll leave you to your cars—just choke me for a bit.” 

Dean’s eyes widened, other hand coming up to run through Castiel’s hair. Castiel planted his hands on Dean’s knees, like he was praying for deliverance. He grinned when he felt Dean’s hand constrict his airway. 

“I saw somewhere,” Dean said quietly, eyes alight with wonder and lust, “that if you start choking someone, and they smile, you were never the one in control.” 

Castiel only smiled wider and closed his eyes as Dean leaned in for a kiss. He was floating again, and he loved it. 

…

 

“So let me get this straight… I leave you at a bar last night, which you said you’d be home from that night… and you show up almost eighteen hours later, with bruises on your neck and a check for rent. Even for you, this is impressive.” Despite her words, Anna did not look impressed. She stood in their dim kitchen with her hands on her hips with one eyebrow raised like Castiel was a naughty third-grader who needed to be disciplined. 

Castiel rolled his eyes. “It’s not like I went off and gambled away all my money. This even covers your half.” 

Anna huffed and reached a hand out for the check. “I suppose it won't matter to Nicole where the money comes from, right? So long as it gets paid.” Castiel watched her blue eyes scan the check, as if she could tell it was fake just from looking at it. “I can't believe you bagged a billionaire. I’m in the wrong business.” 

“Rookie mistake, Anna,” Castiel stretched his arms over his head, relishing the pop of his shoulder. “You don’t bag the billionaire, the billionaire bags you. You gotta make your time seem worth the money.” He slipped past Anna to the fridge, where he pulled out a bottle of water. He offered one to Anna as well. 

She took it and sat down at their tiny table, which was still two milk crates, stacked on top of each other. “Sorry, O Wise Male Escort. I had no idea I was rooming with the patron saint of self-esteem.” 

Castiel shoved her lightly while taking a sip of water. “Come off it. The rent’s taken care of. Maybe we can get some real dinner once in a while.”

“Are you going to be around for dinner?”

“Like tonight? I dunno—“

“Like ever,” Anna said, looking up at him with her eyebrows raised. “It sounds like he wants you to get pretty comfortable at his place. Are you going to live here much anymore?” 

Castiel sat down at the other rickety chair. He pushed his hand through his hair. “I guess I don’t know. I like it there, but you know I’m not going to leave you with the rent to pay.” 

“What about school? Are you going to get time off for that?”

“That’s a long way—“

“And shows. You do art shows. You can make money that way.”

“Anna, I don’t—“

“And for that matter, are you done at the bookstore too?” 

“I don’t know!” Anna fell silent and Castiel fiddled with his water bottle, slowly peeling off the label. Upstairs, a heavy pair of boots stomped around, seemingly frustrated, telling the story of their upstairs neighbor going another day without calling his ex-wife. 

“Castiel,” Anna started, putting her hand on his arm soothingly, “it's not that I don’t support you, because, believe me, I get it. You gotta do what you gotta do. But maybe this isn’t what you have to do to really make it. You still deserve to have a life.” 

Castiel smiled sadly. “It’s not much of a life if most of it is spent on my knees, trying to get enough money for new paints, is it?” 

“This is temporary. You know that. I know that. And anyone that judges you for that is shit.” 

Castiel took a long sip of water. “So what you’re saying is that I need to be careful before I get in too deep with Dean?” 

Anna cracked open her own water bottle. “I’m saying that you need to be careful not to let this rule your life.” 

“But what if I really want it to? He’s nice.” 

“He’s a john, Castiel. I have clients at the club that keep coming back, specifically to watch me dance. And they tip well enough, fine. But at the end of the day, that’s all they are, clients.” 

“I dunno,” Castiel leaned back in his chair. “he might be just a client, but he’s one of the best clients I’ve ever had. I might need to hang on to him for a while.”

Anna snorted and waved the check in the air. “I’ll say. If this keeps up, give him my number, he can order me around too.” 

Castiel rolled his eyes. “Back off, he’s mine. And he’s not just a walking ATM, Anna. He’s got depth.”

“That sounds sexual.” 

“Shut up.” 

… 

With his phone charger and a few changes of clothes in a bag, Castiel started south towards the subway station. Nicole was her usual grumpy self when he entered her office, but she brightened up considerably when she noticed the name at the top of the check that was handed to her for the full amount of the month’s rent. 

How do you know Dean Winchester? she’d asked. How she knew Dean, Castiel wasn’t sure. Everyone in this city seemed to fall to their knees to acquiesce to Dean’s requests, like he was royalty. Castiel hadn’t had the faintest idea who he was before their meeting. 

He still wasn’t sure what Dean’s company did, though… 

While the subway was hurtling into the station, Castiel pulled out his phone and went to Google. He typed Dean’s name into the search bar and was greeted with a multitude of headline about various business dealing involving Dean and several foreign dignitaries. There was an image of Dean, smiling casually in a suit that must cost over four thousand dollars, standing next to one of the princes of the United Kingdom, Castiel could never keep them straight. There were even headlines about an attorney named Sam Winchester, who appeared with Dean in several shots taken by the paparazzi around Los Angeles, Boston, and (Castiel had to laugh) outside of a campy strip club in Vegas. This must be the brother Dean had mentioned. Both men were so handsome and clearly powerful, it was no wonder their company was doing so well. 

While sitting in his seat on the now-moving subway, Castiel pulled up his ongoing chat with Dean. He attached the picture from Vegas.

_Sent >>  
Nice hat. _

Dean’s reply came not a moment later. 

_Received <<  
What can I say, I love lavender cowboy attire. _

Castiel laughed. His phone buzzed again.

_Received <<  
Stalker much? _

_Sent >>  
Maybe I was looking for hat inspiration _

Despite what Anna said about not getting in too deep and obsessing over this new thing with Dean, Castiel couldn't help but find enjoyment in flirting with Dean. The man was magnetic, there was nothing else for it. He was charming, disarmingly funny, and he cared so damn much about the people around him, it was hard not to get a little sucked in. There was nothing wrong with enjoying one’s work. In most work places, it was encouraged even. That Castiel enjoyed talking to and flirting with his client only made his job that much easier. Mutual benefits. What the word Dean had used? Symbiosis. 

Dean replied. 

_Received <<  
You didn’t tell me about this alleged cowboy fetish and I am hurt. _

_Received <<  
Now I have to completely rethink the surprise I had for when you got back _

Castiel rolled his eyes. It couldn't hurt to lay it on a bit thick if he was going for the guise of making his job more enjoyable, right? 

_Sent >>  
Maybe it’s less of a cowboy fetish and more of a you fetish. _

This time, it took Dean just enough time to reply that Castiel got nervous. Maybe that wasn’t the proper way to respond. Sure enough, however…

_Received <<  
Hurry back then… _

Castiel’s breath quickened, which instantly made him feel ridiculous. It was just a text message. No need to get so bent out of shape over something said by the man who paid him for sex. 

Still, the possibilities were tantalizing. 

Castiel was never so glad to see his stop.


	7. Rocket

**Summary for the Chapter:**

> Dean has a surprise for Castiel.

When Castiel first met Dean, he wouldn't have bet anyone that the handsome billionaire would be one for curling up in a blanket burrito on the couch, eating straight out of a carton of Ben and Jerry’s. Sure, the man liked to be comfortable, that much was obvious in the thickly padded carpet, the overly fluffy comforters on every bed, the state of the art entertainment system that Castiel still didn’t even want to think about learning to use. Still, seeing Dean buried up to his chin in a thickly-knitted blanket-tortilla put a smile on Castiel’s face that he didn’t want to examine too closely. 

Dean looked up when he heard footsteps enter the main living room, needing a couple tries to get the blankets out of his face so he could see. His arm, holding the half-empty ice cream container, appeared from the depths of the burrito, offering his treat to Castiel. Plopping down next to Dean, Castiel took the ice cream and the spoon, sitting a safe distance away from Dean on the couch. 

“Have a nice time with Anna?” Dean asked casually, like they were a totally normal couple, seeing each other after a totally normal day of totally normal work. Like one of them wasn’t paying the other to be there. 

Castiel nodded, scooping some ice cream on the spoon and putting his mouth around it. “She was pleased about it. So, thank you, again.” Better to appear gracious about it, than terrified and guilty about getting paid to enjoy something so much. 

“My pleasure,” Dean said, smiling warmly. He gestured towards the television. “You seen this movie before?” 

Castiel hadn’t. The guy on screen was running as fast as he could, while vehicles were exploding on either side of him. He yelled something into a walkie-talkie and was met by static. It could have been any number of movies. Trust Dean to like generic action movies. 

When Castiel shook his head, Dean immediately grabbed the tablet remote and pulled up the guide. Castiel protested, but was ignored and handed the tablet. Dean snatched back the ice cream. “Just don’t pick Twilight or something like that.” 

Castiel snorted, flipping the tablet the right way, "You're just waiting until I leave, so you can marathon it," he teased. 

Dean held up his hands. "I just saw it on the guide, don't blame me for good tv," he teased right back. 

Castiel tapped the screen a few times, highlighting various titles and pulling up menus. “This isn’t a remote Dean, this is a fucking drone that chooses what you watch.” Castiel huffed. He tried to scroll to another channel, but ended up on the Spanish movie channel. It looked like the cast from Die Hard, but Castiel couldn't be sure. 

Dean made a noise of interest, ice cream spoon hanging out of his mouth. Castiel finally got to the guide again, _thank God!_ and scrolled back to the single digits where the channels were more familiar. The movie played on in the top corner of the screen, which Dean seemed to be watching closely. Castiel had grown up in a fairly diverse part of Pontiac, Illinois, which wasn't really saying a whole lot for their part of the state. Still, he thought there was maybe one family in his entire subdivision that even spoke Spanish. He took Spanish in high school, but his teacher had always told him his mouth was better suited for German.

Castiel thought his mouth was better suited for other things entirely. 

Bruce Willis' character said something to the actor that Castiel knew only as Snape, which made Dean chuckle and shake his head, reciting the next line with the actor in perfect harmony. Castiel glanced over at him. 

“You speak Spanish?” 

Dean shrugged. “I picked up a bit while I was growing up. Before Missouri, I had a housekeeper that spoke really broken English. She was cool.” 

Castiel went back to the remote, hurriedly closing a menu that had popped up on screen. He wondered what life would have been like being raised by housekeepers and nannies. “Missouri is nice. She treats you like family.” 

“She is like family. Pretty damn close anyway. She and my mom were really close before she died.” Dean didn't look at Castiel, but a muscle jumped minutely in his jaw. 

“Oh Dean, I—I’m sorry.” 

Dean offered the ice cream tub in exchange for the remote, tugging it out of a grateful Castiel’s hands. “It was a really long time ago, Cas. Sammy doesn't even remember her much, he was so young when it happened.” He picked a channel where Black Swan was playing. Castiel had seen it a few times, Anna loved it to pieces, but he didn’t expect Dean to choose it. 

“My parents both died when I was really young, too.” Castiel said after a moment of silence. He didn't like to talk about it much, not to Anna, not to his uncle, not to anyone. He didn't even really know why he said it now. Perhaps he and Dean had more in common than he originally thought. Dean glanced over at him, and took his hand, smiling softly. Castiel was sure his hands must be cold from the ice cream, but Dean’s were very warm. Castiel found his cheeks getting warm when Dean squeezed his hand, pulling it to his mouth to lay a soft kiss on his knuckles. 

"Guess we both turned out okay, didn't we?" Dean said. Castiel shrugged, and scooted closer to Dean's warmth.

…

Right as Castiel started getting drowsy, settled on the couch, Dean shifted, pulling the blanket off of himself. As Castiel glanced up at him, he realized their hands were still intertwined. 

“Oh, before our movie marathon, I meant to tell you that I missed you while you were gone.” 

Castiel smirked, and tilted his head. “I was gone like two hours.” But if he was being honest with himself, he missed Dean too. 

Dean shrugged. “Still missed you. Had a surprise for you and everything.”

Ah yes, the surprise. Castiel had almost forgotten about it when he found Dean on the sofa. “It’s not a car, is it?” Castiel almost hesitated to ask.

Dean laughed and assured him that no, it wasn’t a car, but that it was an excellent idea. Castiel groaned. 

“Cas, when I found you, you were willing to suck my dick for money, you can’t tell me gifts put you off.” He was smiling the whole time he said it, which took a lot of the sting out of his words. 

“It’s not that, it’s just that you give me so much—it’s hard to reciprocate and—“ He cut himself off. He didn’t want Dean to think that he didn’t value himself and his time. _You’re the prize, make it worth it_ , he told himself. 

Dean rolled his eyes. “Anyway, here’s the deal. I’ll give you the surprise, but you need to pick a safeword.” 

Castiel blinked. “What kind of surprise is this?” 

“It’s completely within the parameters of what you agreed to. And don’t worry, I had Sam look over all the details of the contract. He laughed at me for about ten minutes… but it’s all good.” Dean looked at him earnestly, excitement obvious in his green eyes. Castiel trusted him, no doubt about it, but he could feel the anticipation building into a ball of nervous energy in his stomach. 

“O-okay.” 

“And remember, who has the control in this situation?” 

“Me.” Castiel said very quietly. 

“Sorry, who?” 

“Me.” He said louder. 

Dean nodded. “Don’t forget that. You ask me to stop, and I will. Promise. Now, you need a safeword.” 

Castiel shrugged. “I dunno. Pineapple?” 

Dean grinned and tugged the both of them up to standing. “Let’s go then.” He pulled Castiel down the hall towards his bedroom with all the excitement of a kid on Christmas morning. 

… 

“I’m gonna put this on and if you need me to take it off, just call out your safeword, alright?” Castiel’s vision was blocked out. Dean’s big hands smoothed fabric over the sides of his head and seemed to tie something behind him. A blindfold. 

Castiel jerked involuntarily and Dean whispered soothingly to him. With the light blocked out, Castiel could already feel his other senses heighten immeasurably. His skin seemed to buzz and his ears picked up the minute sounds of Dean’s quiet breathing. 

“Cas? You alright, man?” Dean said again. 

“A-alright.”

“You sure you’re good? Still with me?” Dean’s fingers traced his jaw in a quick zip that left Castiel’s skin sizzling. “You need to safeword?”

“No, I’m okay. Just a little nervous.”

“Good.” Dean said, smile apparent in his voice. He removed his hands from Castiel’s body and walked away, his footsteps hushed on the thick carpet.

Castiel took a deep breath and settled back into the comforter. Dean really did spare no expense when it came to creature comforts like this. Castiel wasn't sure if the blanket was filled with down or what, but he was certain he had never felt a bed this comfortable before, blindfolded or not. 

“Now, I’m going to use this little finger massager thing. And I’m gonna use it on your cock.” Castiel jumped as Dean’s warm palm smoothed over his side. His voice dropped down to a whisper, “It’s gonna feel so good, baby. Is that okay?” 

Castiel swallowed and nodded, knowing Dean would take it as acquiescence to move forward. Dean surged forward and kissed him hard, throwing him a bit off balance, but he eagerly opened his mouth to Dean’s ministrations. He liked knowing that Dean enjoyed kissing him as much as he liked kissing Dean. 

“Gonna turn it on now, lemme know if you need me to stop.” Dean whispered into his ear, nipping at the lobe,

“Dean…” Castiel gasped, thrusting his hips up blindly. Dean was doing that thing where he hovered over him, not quite touching him, but still allowing Castiel to feel his body heat radiating everywhere. He thrust up again, eager to catch some kind of friction against where he was hot and hard, even now, before they had really started. Dean groaned into his neck, allowing himself to press into him, thrusting slowly against him and causing stars to briefly appear behind the blindfold as Castiel’s breath hitched. 

“Gotta stop or this’ll be over before it’s even started.” Dean said, smacking one last kiss on Castiel’s cheek before pulling away. Castiel’s body felt cold without his heat. 

A faint buzz started somewhere to Castiel’s left. He could barely hear it, even with his heightened senses. It came closer, as did Dean’s heat. Dean’s hand smoothed up his leg and hitched it off to the side, spreading Castiel out on the bed. His breathing picked up. 

Dean’s warmth settled between his legs and kisses were dropped on the inside of his knee, leading up to his groin. Castiel could feel how hard he was, his cock must be standing straight up with liquid slicking down the side. A puff of warm air on the head make him shudder and lean his head back against the headboard. He shifted slightly in his restraints, but didn’t pull. 

“Ready?” Dean asked. Castiel nodded violently. He wanted Dean to get on with it and stop this infuriating teasing. Instead of a vibrating sensation, the wet heat of Dean’s tongue washed over his cock. Castiel whimpered. Dean slicked his tongue over the head and down the side and back up and over. Castiel could feel the bastard smile as he pressed his lips over the sensitive skin. 

“Dean! Ah, this isn’t— oh my god, this isn’t what I thought we were… oh.” It felt like a finger. Castiel reasoned that it felt like a finger, because it was a finger. A buzzing finger covered in the most delightful sensations known to mankind and god is this what girls were able to feel all the time when they used vibrators and no wonder they did if it felt this good and—

The litany of babble in Castiel’s head stopped abruptly when Dean nipped at the skin in the apex of his thigh, drawing his attention back to earth.

“You doin’ good, Cas? You’re making some real nice sounds over there.” 

Castiel could hear the grin in Dean’s voice and was sure it was as salacious as Dean could possibly make it. He hadn’t realized he was making so much noise; perhaps the babble wasn't as internal as he thought. 

Then Dean shifted the vibrator so it smoothed all over the head of his leaking cock and all chances of keeping quiet flew out the large bay window. 

Castiel keened for it, arched his back to get more of the sensation, gasped as he felt more liquid slick down the side of his cock. He felt Dean press lush, wet kisses into his thighs and suck until hickeys rose to the surface. Dean’s vibrating fingertip moved down the underside of his shaft, causing him to buck up and whine loudly. 

“Yeah? Sure sounds like you like this, baby. Makin’ so much noise for me, tellin’ me you like it so much. God, you’re so fucking gorgeous like this. And you don’t even know.” Dean murmured while painting his thighs and hips with marks. 

Castiel tugged at his restraints as the fingertip moved lower, almost on top of his balls. Fuck, but Dean was going to make him come with just a single finger and he knew it too. Castiel’s voice sounded pathetic, even to himself, whining and begging for more, and Dean just chuckled darkly and laid another wet kiss somewhere on his body. Castiel wondered how long Dean would draw this out for. Would it last for hours and hours, or would he make it quick? Castiel had the potential to come from just a few minutes of this exquisite torture, it wouldn't take long at all. He was sure Dean would be pleased with him then. He always loved it when Castiel didn't hide how much he wanted Dean. 

He yanked hard against the handcuffs.

“Dean! Dean—need you to— I want—“ 

Dean pulled away from the base of his shaft and pressed the vibrating fingertip lightly into the head of his cock again, just below the slit. Castiel threw his head back and groaned, smacking his head on the headboard. Immediately, Dean’s hand was there, rubbing softly to dispel the stars that cropped up from the collision. 

“Sorry, Cas. You alright? What were you saying, what do you need?” Dean kept rubbing his head, the fingertip massaging into Castiel’s side on his other hand. 

Castiel thrust upwards into where Dean’s body was slung across his. “I want to see you. Please, can we take the blindfold off? I have to see your face.” 

The darkness is replaced by bright light that makes Castiel blink. The halo of light settled around Dean’s perfect face, staring back at him with an expression of awe that Castiel does not understand. He started to apologize for not being able to keep the blindfold when Dean’s mouth was suddenly attached to his. Dean rolled so he was completely touching Castiel everywhere. The buzzing vibrator was still on Dean’s finger, but it was traveling up and down Castiel’s skin, causing his stomach muscles to jump. He pulled at his restraints, he wanted to touch this man making him feel so many good things, but he couldn’t. He had to let Dean kiss him stupid.

“Course you can see me, baby. You’re so good for me.” Dean said, between kisses. Finally, he pulled away and settled between Castiel’s thighs again, breathing heavily. Able to fully see him now, Castiel could see that Dean had stripped his shirt and pants and was sitting in his boxers, his erection painfully visible through the plaid fabric. 

Castiel raised an eyebrow and nodded at Dean. “You want me?” He sounded more breathless than he would have cared to admit, but Dean just did that to him. Dean let his free hand wander down to cup his own erection, biting his lip as he surveyed the man in front of him. Castiel was sure he looked like a sight. His hair was probably a wreck from Dean scrubbing his hands through it and his lips felt as swollen as Dean’s looked. The heat that had been ripping through him had quieted to slow burn. 

“Oh, I always want you baby. I’m gonna make you come so goddamn hard first and then I’m going to take you.” He murmured, barely above a heated whisper. 

Castiel did his best to school his features into what he hoped was a demure expression. He spread his legs and pleaded silently with Dean to resume his activities. He watched Dean take a shaky breath and settle back between Castiel’s thighs, hooking Castiel’s knees over his shoulders. Positioned like this, Castiel felt totally exposed to whatever Dean wanted to do. If he wanted to lick across his hole and make Castiel beg for release, he could. And Castiel would beg. Shamelessly. 

Castiel watched as Dean took his fingertip vibrator and set it ever so gently on the very tip of Castiel’s cock again. He jerked and gasped as Dean slid the fingertip over the head in circles. The circles got bigger, completely encompassing all of Castiel’s cock head and he heard his own breathing kick up into a heavy panting. He tore his eyes away from his cock and looked up to see Dean drinking in his facial expression with rapt attention. Dean smiled softly when he saw he had Castiel’s attention and leaned in to suck a kiss to the shaft of his cock. 

“You’re so close, sweetheart. I can see it. You’re all hot and bothered and you’re ready to come for me like a good boy. You gonna do it?” Dean shifted the vibrator so it trailed down his cock. Castiel felt so hot. His abdomen was tight and coiled, ready to blow like he had never felt before. It was always like this with Dean. He always felt so out of control and dizzy and wonderful. He didn’t know how he was expected to ever let this go. 

He whined. “I’ll come for you. I’m really close. So close.” Dean zipped the vibrator across his balls and Castiel jerked up, almost sitting. He felt the strain of his abs and arms from sitting that way, but he didn’t care. The heat in his stomach was spreading to his face. He was blushing so hotly, he felt like the flames might burst out of him. 

“Yeah? I know you want to come, you’re dying for it, aren't you? So good. Come on sweetheart, let go for me. You’re gonna feel so good when you do, come for me. Come all over my hand, I can see how bad you want it.” 

“Dean—!” Castiel made an abortive attempt at another sentence before Dean pressed right into the head of his cock again, causing the heat to crest up and overtake him. He drew in a deep breath and he curled in on himself and Dean. Come striped up his chest and all over Dean’s hand as his legs shook. He gasped out a mixture of Dean’s name and a long string of _shitshitfuckohmygod._

He was still panting when he fell back against the bed, his hair plastered to his forehead with sweat. Dean ripped off the fingertip vibrator and let it hit the wall before he surged up again to slot their mouths together. Castiel was still restrained in the arms, so he couldn't scoop himself closer to Dean the way he so desperately wanted. Dean sprawled across him, running his hands over every inch of exposed skin. 

“Oh you were so good for me, baby. So fucking hot. And all for me.” Dean thrust against his hip, Castiel could feel exactly how hard he was in his underwear, leaking even through the fabric. 

Castiel pulled back as best as he could. “Dean—Dean, are you going to fuck me now? You said you were going to take me.You gotta fuck me.” He could feel the desperation that must be painting his features, desperation to get this beautiful man inside him as fast as he could. He didn’t care that he was still technically a virgin. He was going to change that right the fuck now. Dean moaned against his shoulder and pulled up. His eyes were wild and dark. He didn’t let up thrusting against Castiel’s hip, and if Castiel hadn’t come so soon, he would have been deeply aroused by the unbridled desire in front of him. 

“Bet you’d love that, wouldn't you? You’d let me fuck you after I made you come so hard your legs were shaking uncontrollably.” He kissed Castiel again, tongue staking a claim that no one would dare defy. “There’s no time. I’m too close. Got so hot watching you enjoy my vibrator. And it was on my finger, Jesus Christ Cas.” With one hand he supported himself as he used the other to yank his boxers down. Castiel helped him with his toes, wiggling the fabric down below his magnificent ass. As soon as his heavy cock slapped up against his stomach, he ground down into the groove of Castiel’s hip. He buried his face into Castiel’s shoulder. Castiel’s previous release, as well as Dean’s own wetness, helped slick the way. Castiel breathed filthy encouragement in Dean’s ear and licked and nipped at whatever skin he could reach.

It didn’t take long, maybe two minutes, for Dean’s body to lock up and for him to come wetly against Castiel’s hip. He slowly reached up and undid Castiel’s handcuffs with more finesse than Castiel thought should be possible from that angle. After the handcuffs fell away, he gently pinned Castiel’s wrists to the headboard with his own hands, running his fingers over Castiel’s palms. He propped himself up on his elbows and traced all the way down Castiel’s arm with just his fingertips. Castiel watched his face but Dean did not look at him. He ran his hands all the way up over his shoulders and across his collarbone. The moment felt extremely intimate to Castiel, but he liked it. The late afternoon sunlight streamed in the window, as Dean apparently had an aversion to blinds or curtains. 

Finally, Dean looked back at Castiel’s face. “Did you enjoy that?” His voice was a bit hoarse but still much softer than his usual tones. 

Castiel smiled and nodded. Dean leaned in and pressed an achingly gentle kiss against his lips. Castiel hugged him close now that his arms were free. 

After a too-short time, Dean pulled back and made to get off the bed. When Castiel protested, he leaned back in and pecked him on the lips. “Gotta clean you up before you fall asleep on me.” 

Dean left the room and was gone for only a minute before he was back, softly wiping down Castiel’s abdomen with a warm washcloth. Castiel hummed under the attention and when the other man was done, he reached for Dean to pull him back into bed. Even though he loved the heat that Dean’s ministrations provided, he loved this more. The closeness, the easy intimacy between them. It was times like this when he did his best to forget that this was only for money and that it would be over soon. Dean turned them so they laid side by side, cuddled into each other’s warmth. 

“Imma go to sleep now.” Castiel slurred, thoroughly exhausted, though it couldn't have been later than two or three in the afternoon. Dean pressed a kiss to his forehead and settled down beside him, throwing a heavy arm over his side.

“I’ll be here.” He said, slightly muffled into the covers.

**Notes for the Chapter:**

> Good evening folks! I hope you enjoy this update; it was a lot of fun to write. Leave a comment or kudos if you liked it, as I love/thrive on positive reinforcement! 
> 
> Also, please note: I have never seen Die Hard. 
> 
> -azo


	8. Painting By Numbers

**Summary for the Chapter:**

> Dean has some brotherly bonding, and Castiel does some school supply shopping.

The term ‘waking up’ implied that there was a clear ending of one activity, and a concrete start of another. ‘Waking up’ meant to stop sleeping, and begin being conscious. For Castiel, he didn’t so much as wake up, as become aware that he was no longer dreaming, and that the warm weight behind him and slung across his side was another person. 

He blinked open one eye, grimacing slightly at the way the late afternoon light was slanting in the window. He really had to do something about the windows in this place. The solid warmth behind him snuffled, ruffling the back of his hair, and tickling him in the process. A grin spread across his face. 

Dean.

Castiel should have done this sooner, should have started selling himself to billionaires sooner, should have given himself this chance to make some money, get taken care of, have really intense-body-shocking orgasms, fall in—

Fuck. 

Castiel blinked, and rolled over to face his sleeping partner. The sunlight was mostly kept out of Dean’s eyes by Castiel’s shadow falling over his form, but the streaks that hit him illuminated the freckles over the bridge of his nose. Castiel wasn’t sure he ever really appreciated noses. Eyes, certainly, held a lot of artistic interest. Not just to him, but to most artists; the eyes were the hardest and most important thing to get right. Still, noses held a lot of importance in a person’s face. While drawing a portrait, the wrong shaped nose could entirely change the portrait. Castiel remembered, back in the early days of the seventh grade, there was this girl that he really liked—no, he wasn't a “gold star gay”, deal with it—but he wasn’t sure how to approach her. He couldn’t even remember her name, now. Fondly, he remembered that what he had liked most about her were her eyes, wide and green, surrounded by thick lashes. She was also the most talented artist in the entire school. Castiel had tried everything to win her over, and at least get her to talk to him. Or—at least everything any other seventh-grade boy would do… He hung out by her locker, in the off chance she might want to talk to him, he tried—and failed—three times to work up the nerve to ask her to the Valentine’s Day dance, he even went to her track meets, waving whenever he thought she was looking his way. Castiel had to face it—he was a bit of a helpless dork in those days. The act that had finally caught her attention was when Castiel drew her portrait in a fit of need to impress the pretty girl. Castiel worked day and night for almost a week sketching, blending, and erasing. Trying to get it perfect. Trying to make it worth the effort. The trouble was that Castiel had never done a portrait up to that point. Honestly, it wasn’t half bad, even now in Castiel’s humble, more educated, more experienced opinion. 

The nose though.

Castiel still remembers the look on her face, Haley, he finally remembered. The way her kind face had crumpled, ever so slightly, in an attempt not to laugh. To this point, Castiel still wasn’t sure he had ever gone so red so quickly. He knew the nose wasn’t right, couldn't make it look right, no matter how many times he erased and tried again. He knew, and he still gave it to her, eager to hope she’d appreciate the thought. And truly, when he was looking at it propped up on her desk from his spot on her bed, it looked more like a slightly squashed tomato than a nose, but… the hickeys on Castiel’s neck at supper that night said that Haley had more than appreciated the thought anyway. He did stop drawing portraits after that, though. No matter how pretty the person was. 

Presently, Castiel reached out a thumb to brush down the straight angle of Dean’s nose. There was the slightest bump on the bridge, almost unnoticeable. The tip upturned in a way that made his entire face look more boyish. And a bit crooked. Castiel smiled. For all that Dean’s face was remarkably, almost annoyingly symmetrical (save for the crooked grin) his nose was a bit off center. Castiel wondered if maybe he’d been hit in the nose when he was younger, maybe by a baseball. Maybe by a fist? Maybe Dean had been a troublemaker when he was young. Castiel snorted. That wasn’t a maybe. Dean had _definitely_ been a troublemaker, and still was. 

Dean’s nose twitched slightly, awoken by Castiel’s attention. Castiel pulled his hand back under the covers. Briefly, he considered pretending to be asleep, but quickly tossed that idea aside. A coward, he was not. 

Blinking a few times, Dean focused on Castiel, mouth curling upwards. “Guess we needed that, huh?” He sounded groggy, and a bit on the verge of a yawn. 

“You didn’t fuck me. You promised.” Castiel couldn't help but feel petulant, even if most of it was for show. 

Dean rolled his eyes, pushing himself onto his back. “I didn’t know it was such a priority.” He glanced over at Castiel. 

Shrugging one shoulder, Castiel scooted a bit closer. Sue him, he was jacked off spectacularly by this man not three hours ago—he’s gonna be a little clingy. “I just—we haven’t done it yet.” 

“And you don’t think we’ll get there eventually?” Dean wasn't smiling. Castiel didn’t like that. 

He moved and propped up his head on Dean’s chest, taking a liberty he wasn’t quite sure he was allowed. Still, Dean didn’t stop him, and readjusted to make himself more comfortable to lie on. Castiel laid on his folded hands. “Sometimes I wonder.” Castiel smiled to take the heat out of his words, making them into a playful jab. He didn’t want Dean to be mad at him for wanting to hurry. 

Finally, Dean slipped his fingers across Castiel’s back, running up the knobs of his spine. Again, Castiel was made aware of how thin he must seem under Dean’s hands, lean by force, not by option. Castiel pressed his lips to Dean’s chest beneath him, causing Dean’s breath to hitch minutely. “Y’lucky you’re cute.” 

Castiel leaned forward to hover his mouth over Dean’s. “Later, though?” 

Dean reached up to meet him halfway, but Castiel kept his mouth out of reach. “Yeah, yeah—promise. Just, get down here.” 

Castiel recognized the cop out, being brushed aside, but he was more than willing to take advantage of Dean’s attraction to him. Especially for this. 

They made out lazily for a few minutes, enjoying the quiet and the warmth of the sun still coming in the window. Impulsively, Castiel reached out and pinned the hand that wasn’t skimming up and down his back to the bed above Dean’s head. Dean arched up underneath him, gripping his hips with one hand to pull Castiel’s body more fully across his own. 

“Oh, you like that don’t you?” Castiel raised an eyebrow, enjoying the change of power here. It wasn’t often that he was the one in charge of… well, anything. 

Dean had a wild look in his eye. “Well, learn something new every day?” He ground up against Castiel again.

Castiel grinned. This was ridiculous, even for him. They just made each other come—really, really hard—a few hours ago, and here they were again. This was rare for Castiel. Usually his johns weren't quite so enthusiastic to be around him for too long. Even though they took his services willingly enough, even demanded them at times, there was something about the idea of paying for sex that made them run away pretty quick after. 

Shameful. 

If there was anything shameful about how Dean treated him, it was in this. In how good it felt to be employed and servicing this man. And it had a hell of a reward. 

Castiel pressed down on Dean’s wrist, silently telling him to keep it there. He pulled Dean’s other hand off his back to join it’s twin above Dean’s head. When he was satisfied with Dean’s position, Castiel cradled both hands around Dean’s jaw, opening it wider, making it just a bit dirtier, a bit wetter. He tangled his tongue with Dean’s, feeling how their lips pulled at each other, equals in this, if nowhere else. He bit down on the man’s lip, pulling a low whine from him. It was science. Bite here, get this sound. Lick there, feel Dean’s hips crest up to flirt with his. Here, straddled across his lap, Castiel felt powerful and excited. 

It couldn’t last however. A knock came on the door, followed by a soft, “Dean?” 

Missouri. 

Castiel liked the woman, thought she could have a wicked sense of humor when she wanted to, but he really hated her right now. The way that Dean let his head fall back into the overly fluffy pillows told him that Dean was having similar thoughts. 

“Yeah, hang on Missouri.” 

“Don't get up on my account, sug,” Missouri said. Castiel ground down a bit more to prove how up Dean already was. “It’s just that you’ve got company in the sitting room.” 

Dean met Castiel’s confused look with one of his own. He shrugged. 

…

Sam Winchester thought of himself a bit more open than his brother. They both went to college, nice colleges, too, thanks to their mother’s inheritance, but while Dean opted for the stuffy halls of Harvard, Sam lit out for the West Coast where the streets were wider and more colorful, and the people were a lot… weirder. 

And, too, Sam Winchester also thought of himself as more grounded than his brother. By no means did either Dean or himself have an easy childhood. Losing their mother so early left their father in such a state of despair that he died of a broken heart not three years later. They had been wealthy before the death of their parents, trust fund babies on a massive insurance company’s dime, but with Dean’s willingness to risk more than he probably should, and Sam’s good common sense, both Winchesters found themselves in a position where they had more money than they knew what to really do with. 

With all of this, Sam Winchester was a bit more than surprised when his brother sidled into the sitting room of his ridiculous lakeside mansion wearing an even more ridiculous bathrobe, and sporting a massive hickey on the side of his neck. 

Raising an eyebrow and gesturing with one finger, Sam chuckled. “What’s going on? Sleep late or something?” 

Dean rolled his eyes good-naturedly. “Gimme a break, I was busy.” 

“It’s nearly five o’ clock in the evening.”

“Okay, so I was really busy.” 

Sam’s face changed, and he cocked his head to the side. “Is that a hickey?” 

“… get out.” 

He threw his head back and laughed. “Oh, so that contract was serious then? I was sort of half-hoping you were just being gross to freak me out.” 

Dean crossed his arms and sat on the arm of the chair opposite Sam. “Did you just come to make fun of me?”

The tiny smile threatening to cross Dean’s face told Sam that he wasn’t nearly as pissed as he pretended to be. The two brothers hadn’t seen each other in a few weeks, between Sam’s court schedule and Dean’s apparent new… hobby. 

“I actually came to see if you were up for dinner tonight… but if you’re too busy with your boy toy, I can come by tomorrow.” The more Dean tried to frown, the wider Sam’s smirk got. 

“Lemme go change and I’ll ask him what his plans are for the evening.” Dean stood, and slipped out of the room, hand rubbing at the side of his neck self-consciously. Sam laughed again and was rewarded with his older brother flipping him off. 

When Dean returned a few minutes later, he had changed into nice jeans and a henley, similar to what Sam himself had on. 

“Boyfriend staying in tonight?” He couldn't help himself.

“He’s not my boyfriend.” Quick, reflexive. 

Sam raised an eyebrow. “I know he’s not your boyfriend.” 

“He’s—uh… he’s gotta work tomorrow anyway.” Dean checked his back pocket for his wallet, and motioned to Sam that they should get going. Sam followed Dean down to the garage to the auto bay. He remembered laughing hysterically the first time Dean brought him here, and showing off his “bat cave” as he called it. Despite Sam’s incessant teasing, Dean was really proud of his garage. Sam was just glad to see his brother happy. 

They walked past a few motorcycles in pieces, which Dean claimed to be fixing. Sam was suspicious that Dean was actually working on his own version of Frankenstein down here. “So what kind of day job does a man who gets paid to be spoiled by you have?” 

“He works in a bookstore, for your information.” Dean still sounded snippy. Sam figured he better tone it down if he wanted any juicy details. The contract hadn’t actually been all that telling of the dynamic of their relationship. All Sam knew was that Dean had a guy tucked away somewhere that he (apparently regularly) showered with gifts, in exchange for blow jobs. “What are we thinking for tonight? The Camaro or the Impala?” 

“Like you would ever cheat on your car.” 

“Damn straight.” Dean flashed a smile and slid into the black behemoth. It was his favorite car, even next to the shiny canary yellow Camaro, and the hot rod red Corvette. Dean loved cars, it was sure, but there was only one real vehicle for him. 

The entire ride to the Roadhouse, Sam tried to pry information out of his brother. Castiel was an art student, he came from Pontiac, he liked his pancakes with honey instead of syrup. Sam didn’t even know what Castiel looked like. 

Pulling up to the familiar wooden front of the Roadhouse, Dean cut the engine and leaned back. “I dunno, Sammy. I like him, you know? I dunno—I feel like I don’t know hardly anything about him.” 

Sam looked out the windshield a moment. There was silence between them, but it wasn’t uncomfortable. Finally, he said. “Sarah and I are trying for a baby." He kept his gaze firmly on the blinking sign advertising keno on the big window of the bar. 

Dean punched him hard on the arm, smiling. “Guess I don’t know hardly anything about you either. What the hell, kid?” 

“We’ve just started trying, so don’t get too excited yet.” 

“Still.”

“Yeah…” 

When they finally made it inside the Roadhouse, Ellen was standing right inside the door, rolled up newspaper in hand. She smacked them both—“Ellen, what the _fuck_?”—and herded them towards a booth. She stood with her arms crossed, glaring at them both in silence for a second, before stalking off to the bar. 

“Did you call her on her birthday?” 

“No—I thought you did.” 

“Shit.” 

She came back with two longnecks in hand, which she set on the table, and scooted herself into the booth alongside Sam. “You know the last time I saw you boys was over four months ago and you couldn't even do me the decency of a phone call. What the hell was I supposed to think?” 

Dean scooped up his bottle and took a long sip. Wiping his mouth on the back of his hand, he said, “Sorry, we got busy. You know, being adults and shit.” 

“No excuse for the woman who practically raised you, Mr. Fancy-Pants. Who makes those jeans, Armani?” Ellen raised her eyebrow.

“Calvin Klein,” Dean shot back, winking. 

“How have you been, Ellen?” Sam said, trying to gain back points. 

She turned to him. “Same old, same old, I guess. A little birdie told me you went and got yourself promoted.” 

Sam chuckled. “I’m hoping to make partner in two years.” 

“And you, Dean? Still keeping out of trouble?” 

Dean raised his bottle in a salute. “Always do.” 

“Dean’s got a boyfriend.” Sam teased, sing-song. He felt a kick under the table.

“It—come on.” Dean’s face had two pink spots high on his cheekbones. 

Ellen’s eyebrows hit her hairline, and her mouth curled up. "Does he now? Well, since I know he won’t tell me about this Prince Charming himself, you’ll have to do it for him.” 

Sam opened his mouth, but Dean interrupted “—he’s in school to be an artist. He paints big pictures of eyes and shit.” 

“An artist, huh? How’d you hook up with him?” 

Dean looked like he was under the inquisition of a nosy parent. “In a—in a bar.” 

“S’it serious?” 

Dean shrugged, taking another pull of his beer. One of the cooks hollered from back in the kitchen. Ellen stood to leave. “Take care, boys. And really… I got a phone.” 

They bid Ellen farewell as she went stomping back into the kitchen, the sounds of clattering pots and pans echoing out into the rest of the bar with the swing of the door. 

As soon as she was out of sight, Dean punched Sam hard in the arm. “Why’d you bring that up in front of Ellen? He’s not my boyfriend.”

Rubbing his arm, Sam chuckled. “Really? ‘Cuz you’re getting all bent out of shape like he is.” 

“Well, he isn’t. He’s… I’m just helping him out with stuff… in exchange for… stuff.” 

Sam leaned back in his seat. “Oh my god.” 

Dean raised his hands, already trying to keep the situation calm. “Sam—“

“Oh my _god_ ,” Sam reached his hands out in front of him, like he was bracing himself on the table. “You’re his sugar daddy! That’s why there was so much in that trainwreck of a contract about gifts and—you’re paying his way through school.” 

“It wasn’t a trainwreck. I didn’t think I did half-bad.” The contract was, in fact, a bit of a trainwreck.

“Just tell me he’s not a minor.”

Scooping his hand through his hair, Dean looked around at the other patrons of the bar. Ellen looked over and raised an eyebrow. “Jesus, Sam, no. He’s super legal. Could you keep it down—“

Sam dropped down to a whisper. “How does that even work? Does he live with you?” 

“Okay, look. It’s still pretty new. I pay his rent and stuff, and he—you know. Yeah, I’m gonna pay his tuition, but Sam. You gotta see what he paints. He showed me pictures and stuff, and he’s… he's incredible. He’s good. Really good. Better than mom, even.” 

That made Sam pause. He and Dean didn’t know much about art, they never really got into it in school, and by that point, their mother had already long since passed away. Still, if this Castiel’s work was comparable to their mom’s by Dean’s standards… “You’ve seen his work in person?”

“I—no, what? I’ve seen pictures.” 

“How do you know he’s not just scamming you for your money?” 

Dean’s face was an ice sculpture. “Cas wouldn’t do that. He’s a good person.”

“He’s taking money for sex.” 

“Yeah, but he wouldn’t do that. He just wants to go to school. I’m just… helping him.” 

“Paying his rent, paying his tuition, and anything else he might want?” 

“… yes.” 

Staring at his idiot brother across the table, Sam let the breadth of the situation roll around in his head. “And that doesn’t seem sketchy to you?” 

“This isn’t the first… relationship like this I’ve had, you know.”

Sam raised an eyebrow. “Oh, you’re a seasoned sugar daddy?” 

“No—just… this is why I made a contract. I know it’s not legally binding or whatever, but this way… everyone knows what their getting up front. There’s no guessing, there's no wondering. He needed the money, and… I like him." Dean looked down at the table and fiddled with the label on his beer. 

“I just don’t want this to turn into something bad for you.” 

Dean looked up, earnestly. “Dude, you and me both.” 

The brothers fell into silence again. Dean turned to the television above the bar, apparently trying to lose himself in the rugby match on the screen. Sam wasn’t sure Dean even knew how rugby was played. “So he’s going to art school?” Sam could be supportive. Clearly this was important to Dean, and he could be a good brother and not make this worse for Dean than he was already making it for himself. 

“Yeah, up at the Institute.” 

“And he’s starting again in the fall?”

Dean looked down, but still seemed unable to meet Sam’s glance just yet. “Think he’s supposed to graduate in the spring.” 

“Have you taken him school supply shopping yet?”

Finally, he looked up. “What?” 

Sam let a teasing smile play across his face. “Come on Dean. What kind of sugar daddy are you? Can’t let your sugar baby walk into the first day without an apple for the teacher.” 

“Stop, you’re making this way dirtier than it has to be.” 

“You’ve gotta be kidding me.” 

…

“He said what?” Castiel was really torn between amusement and annoyance. Amusement that however Sam approached the situation was apparently doing a great job of making Dean blush, and annoyed that Sam was inserting himself into his—their business. 

The two men walked down Jefferson Avenue, the whole street seemingly in a hurry. Not that it was a strange feeling in Chicago. 

“He said… that I should ask you to paint something.” 

“To prove I’m not scamming you out of your money.” Oh, but Castiel was the master of sarcasm. 

Dean shrugged, eyes on the pavement, shuffling his feet. “Not in those words exactly…” 

This particular art supply store, Jameson’s, was a rarity in Chicago, in that it sold big canvas. Huge canvas. Big enough that it wasn’t really practical to carry back with you on the bus, so you’d better have alternative travel plans, or be willing to wait for the two-week delivery. The dark-stained wooden doors gave way to a coolly lit warehouse, stacked to the very brim with every sort of art supply a person could want, and several they would have to ask about how to use. Jameson’s was famous for their color selection of oil paints as well. Everything and every kind of formula available. Dean had mentioned supplies for the upcoming year when Castiel arrived the next morning after his and Sam’s “outing,” and Castiel had shrugged, replying that he usually picked up whatever he needed at the school store when it went on sale. Upon hearing this, Dean grabbed his keys and ushered Castiel to the auto bay, and here they were. 

Castiel pulled up a list of class supplies on his phone, clicking through to his intermediate-level painting class. He headed towards the brushes, and heard Dean follow with a cart. “So what do you want then?” He didn’t look at Dean, but instead focused on the rows of brushes in a higher quality than he ever could have dreamed of affording on his own. He definitely needed a new filbert. He picked up a Gamblin short brush and tested the give of the bristles. Definitely too springy for oil paint. 

“What do you mean?” Dean asked behind him. Castiel chanced a glance at him, and saw him staring up at the display of watercolor brushes, mouth agape. 

Castiel put the Gamblin down and picked up a Grumbacher with a long silver handle. “I mean, what do you want me to paint? I can’t really do cars very well, but I can try.” With a nod, he passed the Grumbacher to Dean, who placed it in the cart without looking at it. His class list also called for a bright, but Castiel was reasonably certain the one he bought six months ago should be in fine condition for class. 

“You’d paint something specifically for me?” 

Castiel looked over at him. Dean’s focus was entirely on him now, with an expression of disbelief. “Sure,” he said easily. “I like doing it, and it’s fun to paint stuff for people.” 

“What if I wanted something big to hang over my mantle?” 

“I’d ask which mantle, because you have like, three.” 

“The main one, then.” 

“Sure.” Castiel said with a smile. He tugged lightly on the cart to move them to the oil paints. He picked up a few tubes of Windsor & Newton. It wasn’t the best brand, but Castiel felt a certain degree of loyalty to these paints. They were what he learned on, after all. He picked up a bound set of quinacridone magenta, cadmium yellow, and phthalocyanine turquoise. This was how you made real colors. Bright, vivid hues that gave the canvas light and the ability to spark up any surroundings. He turned to Dean, “Yell if you see an ivory black anywhere, I need that and some linseed oil. I should have enough white at my apartment to last me.” 

“Isn’t ivory… white? Why would it be in black?” Dean searched the rows of paints as he was told however. “Is it gray?” 

Castiel chuckled and spotted the correct tube, holding it up for Dean to see. The tube was indeed black, but held up next to Mars black, a truer black, a subtle lightness in the ivory was easy to see. “Kind of. It’s a bit harder to mix with other colors, because it tends to make them a little muddy, instead of darker. The painting professors at the Institute are pretty traditionalist though, so we do what we can.” He threw both the ivory and the Mars black into the cart. 

Dean picked up both tubes again and squinted at them. “That’s so weird. They’re both black… but like… not.” 

This was fun for Castiel. Not that Anna hadn’t been fun to shop for art supplies with, but Dean had so many questions. What made brush companies different? What the hell was gesso? What was his favorite type of paint? Castiel ranted about how long oil paints took to dry, and the painstaking process of mixing the pigment, and how acrylics were so much easier to work with but got a bad rep because they were considered less “professional.” He told Dean about the importance of using a fixative that wouldn't yellow when the painting was completed. He lamented how hard it was to keep purple pigment on a painting for more than a year, because the sun just did funny things to paint on a canvas. Dean picked up a tube of metallic gold pigment and tried for three whole minutes to convince Castiel that he needed it. Castiel replied that if he wanted to use that much gold in one place, he’d wind up being another Kilmt, and the world wasn’t ready for that. Still, he didn’t argue when Dean tucked the small bottle in the cart carefully alongside his other supplies. They walked past a display of pottery wheels. Dean asked his opinion on ceramics, and Castiel replied that he’d always wanted to get better, but he hadn’t been able to get into the intermediate throwing class for about two years running. 

Castiel liked when his job was easy like this. Easy to laugh and joke with Dean, easy to just be with him in the same space, easy talking about things that he loved. 

At the counter, the bored-looking girl with shockingly bright purple hair managed to only gape a little as Dean whipped out his card for the staggering amount displayed on the till. Afterwards, he filled his hands with the bags that Castiel did not immediately grab and gave the girl a wink as they left. They started back down the street to the garage where Dean had parked his car, a Chevy Impala, he had told Castiel. 

“What about some eyes?” 

Castiel raised an eyebrow. “What now?” 

“When I first met you, you said you painted eyes, right? Big ones?” 

Nodding, Castiel stepped in the elevator of the garage. They parked on level two. 

“I want a big painting of some eyes. Not like random eyes. A set of eyes.” 

“Like a face?” 

Dean grinned. “Yeah, but just the eyes.” 

“Won’t that look kinda creepy if you have a giant painting of some eyes above your mantle?” Castiel couldn’t help but smile at Dean’s enthusiasm, however. 

“Then don’t make them look creepy. Simple as that.” Dean actually stuck his tongue out at Castiel. 

“Well,” Castiel pretended to think about it, like he wasn’t already planning on agreeing to whatever this man wanted. “I’ll need some space to work.” 

“We can clear you out a space in the garage! You can work right next to me.” Dean sounded like he had been thinking of this for a while. 

When they were seated in the car, Castiel leaned forward quick and pressed his lips to Dean’s chastely. He stuck out his hand, “You’ve got a deal, good sir.” 

Dean smiled, and batted his hand away, leaning in for a proper kiss.

**Notes for the Chapter:**

> Well, lookit the time, folks. It's nearly 2am, but it's on the actual day I said I was going to update! 
> 
> A note about all the weird paint names: the colors listed are actually the colors that I use to paint pretty much everything. They create brighter colors, and more variety than what you would think you would get from a primary red, yellow, and blue. Practically any color in the world you could ever want can be made with a combination of these three, plus white or black. That's why a printer uses these colors! 
> 
> If you're looking to get more into painting, I highly recommend using acrylics. They blend so much easier, and dry faster, giving you quicker results. They're also readily available at almost any craft store. Just make sure to get the actual color name of paint, not a hue of it (e.g. - cadmium yellow, instead of cadmium yellow _hue_.)
> 
> Thank you so much for reading! I love reading your comments!
> 
> -azo


	9. Tighten Up (On Your Reins)

**Summary for the Chapter:**

> Sometimes, progress is two steps forward, and one step back. But that does mean you are not going somewhere.

Things must have been going too well for too long. Castiel should have recognized his luck when he had so much time with Dean, uninterrupted. For the most part, they lived in their own little bubble. No one bothered them, Bobby and Missouri only came and found Dean when they absolutely needed him or when it was time for meals, and there was no one to gawk at them as they discovered the dynamics of their still new relationship. No one to wonder why a kid who still faltered at the amount of silverware that went on a standard table setting or how to work the television in the living room was spending so much time plastered to Dean’s side. 

But all good things had to come to an end. 

“The end” came in the form of a sandy-haired man with a permanent grin etched on his face and a lollipop in his right hand. He introduced himself as Gabriel, but Castiel snorted at how little the man in front of him seemed to live up to the angel of the lord who delivered Mary the good news. Gabriel showed up while Dean was in the shower one afternoon, cleaning up after a rather enthusiastic round of dry humping that had just happened to take place on the floor of Castiel’s makeshift painting studio. Castiel either needed to change the drop cloth, or be constantly reminded of Dean’s strong arms caging him in against the floor while they rutted into each other. 

Gabriel sat across from where Castiel stood in the main foyer. Silence hung over them, dense and awkward. Castiel had just come back from telling Dean about his guest and, with nowhere else to go, sat back down with that very guest. 

“So you’re a… nephew?” Gabriel asked after a long moment, eyebrows raised in some innuendo Castiel did not catch. 

Castiel wasn’t sure how honest he should be with Gabriel, the CFO of Dean’s company, and apparently, his right hand man when it came to anything related to Winchester Holdings. “No,” he finally said. 

“Well, I’ve met the other Winchester brother, so that’s out of the question, and I thought I knew all of his friends.” 

Castiel pursed his lips. He thought after everything, he might consider Dean a friend at least. “No, Dean and I met… not that long ago.” Truly, he hadn’t even intended to be in the same part of the house when Gabriel showed up. He just… appeared. 

Gabriel surveyed him for a moment longer. Slowly, his mouth widened in a grin Castiel could only describe as ‘manic’. 

“You’re a hooker.” 

Castiel blinked. “I—well.” 

The grin on Gabriel’s face was absolutely gleeful now. “Hoooooooo boy. Dean-o has really got himself in some trouble this time, hasn’t he? Tell me, did he come looking for you, or were you trolling for a sucker and came across him?” 

“It was by mutual agreement—“ Castiel sounded defensive, event his own ears.

Gabriel chortled. “Sure, I can’t even imagine how that conversation went. Actually, I can.”

“Mr. Milton, this isn’t really your business… at all.” 

Gabriel held up his hands. “Say no more. Not my place, I get it. Just make sure you do your job, kid. You’ve got one job here, and I’m guessing it isn’t house-sitting.” He finished with a wink, right as Dean came in the room, freshly showered. 

“You tryin’ to get Cas to watch that castle of yours while you go to Vegas again?” Dean asked, shooting Castiel a wink. 

Gabriel looked glum. “He said no, on account of his secret attachment to Missouri’s exceptional cooking. Speaking of which,” he perked up again. “Where is she? Think she’ll whip me up some lunch while we go over numbers?” 

Dean slapped him on the back and sent him into the kitchen, where Castiel heard him greet Missouri with raucous affection. Missouri returned in kind. Dean turned to Castiel. “I forgot he was coming over today. You good doing your own thing, or do you want me to drive you home for a bit? It won’t take long.” 

Castiel assured Dean he would be fine in the garage if he was allowed to stay, and tolerated the quick kiss to his forehead before heading down the hallway, leaving Dean to his business dealings. 

As he entered the deadly quiet garage, Castiel was processing what Gabriel had said. It wasn’t that he regularly took business advice from random assholes. But Gabriel was right. He did only have one job here. It often felt like more of a privilege than a job, but it still was just that—work. Paying the rent. He and Dean fell so easily into each other, but for what? At some point, Dean would grow tired of Castiel and his list of bills, and he’d cut Castiel loose. Then where would he be? 

Castiel wandered over to his corner of the garage and stood in front of his canvas. Progress on Dean’s not-commission was going well so far. He had finished up the basic sketch earlier today, working for hours to tweak the graphite lines until he was satisfied with them. He could start with the base painting soon. The eyes still looked rather spooky, staring blankly out of the white canvas with no real definition. They looked flat and empty. 

Castiel picked up his sketching pencil and gum eraser and tilted his head, looking for places to adjust the lines. Maybe he should stick more to the contract that Dean had agreed to. An actual submissive to boss around, rather than a live-in boyfriend. Castiel was still rather inexperienced being a sub, but he was sure it wasn’t meant to be rocket science. Just had to listen to what the dominant wanted and do it. He trusted Dean with his body, trusted him like he had no one else before. In theory, it should be easy. He had to do the job he was here to do. He erased a line delineating the border of the iris, penciling in lightly a rounder shape, giving him more room to play with the texture of the inside. 

He had to try to be good. 

…

When Dean came down an hour or so later, Castiel was fully involved in his work. He had started blocking off sections of the painting and writing in extremely light print the colors he wanted in that section. When Dean turned on the stereo, blasting out an old song that Castiel was pretty sure was by a band called The Outfield or something. He had heard it several times in the car with his mother. 

Startled, Castiel whipped around, pencil tucked behind his ear, to the sound of Dean laughing at him. Dean pointed to Castiel and shook his hips, mouthing the words to the song. He spun around and grabbed a wrench, singing into it like a microphone. Castiel chuckled and shook his head. 

This man. 

Performing for his invisible audience the entire time, Dean danced over to his latest project, the radiator on the yellow roadster in the corner, and bent over the hood, still shaking his ass like he was in a music video. Castiel rolled his eyes and tried to get back to his painting. 

Castiel had spent some time in some unproductive work environments. Public school in Pontiac, freshman and sophomore year at the Institute, Chicago in general… all terrible places for extended periods of focus. However, sequestered away in Dean’s garage with the man himself for two whole hours, blasting what Castiel could only call “dad rock”, and trying to paint while Dean would rather distract him… Castiel couldn't remember ever being so distracted. 

Dean wasn’t even saying anything, he just happened to catch Castiel’s eye whenever he looked up and shot him that devastatingly handsome smile that would put Castiel off for several seconds. 

Castiel had had enough. He set his pencil down and stalked over to where Dean had taken a short break on the couch. Dean watched him approach, first with a smile, but with confusion as Castiel did not join him on the couch, but instead walked around the back of it. Dean craned his head around to look at him, but Castiel just brought his hands up to Dean’s shoulders and ran his hands all over Dean’s t-shirt covered skin. He still had the wrench in his hands, and he was clutching it tightly. He had a lot of tension in his shoulders, but Castiel was determined to fix that. 

“Hey Cas… w-what are you doing?” 

Castiel smiled at the hitch in his tone, watching Dean’s grip on the wrench slacken. He dug his fingers in, rubbing firmly over the shoulder blade. This was as much for Castiel as it was for Dean. Dean got the tension worked out of his ridiculously nice shoulders, and Castiel got to put his hands all over those same shoulders. Castiel watched a shudder work its way down Dean’s spine. He scooted in close so Dean could feel his body heat all along his back. Dean tipped his head to the side as Castiel ghosted his lips down the strong column of his neck. Dean’s adam’s apple bobbed tantalizingly and Castiel couldn't help but bite down a bit, causing a gasp.

“That feels… uh—good.” 

Castiel smiled, knowing Dean could feel it and knowing that Dean probably had an idea of what he was doing. “How was your meeting?” he asked, light and casual. 

Dean swallowed again. “Good, it was good. Gabe, he—he wants to do something where we… oh—” his voice was muffled as Castiel pulled his shirt over his head. His skin felt hot under Castiel’s hands.

“Yes? He wants to what?” Castiel guided Dean to lay down across the couch, clambering around the couch to sit astride his waist when he was horizontal. He leaned down to brush his mouth over Dean’s spine, practically feeling the electricity zip up and down. Castiel decided that he liked Dean like this, underneath him with nowhere else to be, and nothing else to do. He ran his hands all over Dean’s back, not even pretending to be giving a massage anymore, just making Dean feel good. 

“I—he wants to start a charity of sorts… oh wow… but he doesn’t know what cause to back… Jesus, Cas.” Dean sounded choked up as Castiel buried his face in his neck, nipping lightly. Castiel felt as Dean moved his hips into the couch. Popping his head up, he saw that Dean’s hands were thrown over the side of the couch and clenched into fists. 

“What are some of your ideas?” Castiel asked breathily. He traced his hands up Dean’s arms, loving the muscle there, and deliberately ground his hips down into Dean’s ass. His body was completely blanketing Dean’s now and the temperature in the garage seemed about thirty degrees hotter than usual. 

“Got a lotta ideas that aren’t exactly about my company, sweetheart.” Dean growled, turning his head to get at Castiel’s mouth. 

Castiel pulled back. “No, you’ve had a long day, Dean. Just let me do this.” He sat up again, feeling cold no longer pressed against Dean’s back, and resumed his massage. He hadn’t meant to let them spiral away into lust quite that quickly, but both of them found it hard to keep their hands to themselves. Castiel guessed he wouldn't get any straight answers about the charity from Dean right now. He rubbed at Dean’s shoulders, chuckling as Dean arched up into it like a cat. How had he ever thought this man was detached and untouchable was beyond him—he was clearly aching to be touched. 

“S-sure… _oh my god_ , right there.” Dean was panting and thrusting down into the couch to relieve some pressure on his cock. Castiel grinned and ground right back down into him. 

He leaned in real close to Dean’s ear, “Why don’t you order me around more?” 

“Huh?” Dean answered, sounding completely wrecked. 

“You’re my dom, after all. That’s what's in the contract, right? You’re over here playing sexy mechanic and I. Am. Suffering.” He punctuated each word with a direct thrust into the dip of Dean’s spine, causing another full body shudder from the man underneath him. “Push me around or something.” 

It took a few seconds for Dean to find his voice. “Do you really want me to order you around?” 

“Yes.” 

Dean struggled to roll over until Castiel got up and helped him. When he was on his back, Castiel settled back above the impressive, but obscene bulge tenting Dean’s jeans. “What do you want me to order you to do?” he asked. 

_“Anything.”_

Castiel watched the punch-drunk look clear out of Dean’s eyes, and it was replaced by a hard look that had Castiel’s abdomen tightening up and his cock jerk. 

“Get down here and kiss me.” Dean ground out, a tendon in his neck fluttering. When Castiel’s mouth met his, it was nothing like the achingly sweet kisses he and Dean sometimes shared. This was raw power, barely contained. This was hands clenching around biceps, hands pushing Castiel’s ass into Dean, hands everywhere. This was Castiel feeling utterly powerless to stop whatever was going on, if he’d even wanted to. This was heat racketing up another three notches between them roiling all underneath Castiel’s skin. This was hair-pulling, and sloppy lips, and Dean completely owning him.

Animalistic. 

When they pulled away, they were both gasping for breath. Dean put his hands on Castiel’s chest and pushed. Castiel nearly tripped over himself and struggled to right himself, fighting the urge to cover his hard-on with his hands as he stood in front of Dean. 

Even with his own impressive erection, Dean sat up and leaned back against the couch, spreading his legs and sitting like a king on his throne. His scorching gaze tore up and down Castiel’s body, before he reached out and smoothed a big, hot palm up Castiel’s stomach up to his chest. 

“Take this off, and then on your knees.” Dean pinched a nipple lightly and removed his hand, leaving Castiel to whip his shirt off over his head and sink to his knees in front of Dean. He reached up to place his hands on Dean’s kneecaps, but hovered for a second before putting his hands down. He didn’t have permission to touch and he only had one purpose here. Gabriel’s words echoed in his mind. 

Dean lazily unzipped his pants, letting the head of his fat erection peek through the hole. He swung his head to either side like he was checking if the coast was clear. Slowly, and keeping his gaze trained on Castiel the entire time, he started stroking. Castiel fidgeted. He couldn’t wait to get that cock in his mouth. This, he knew he was good at, everything he’d done in an alley with faceless men, every time a man had whipped out his wallet and his dick in the bathroom of a seedy bar, that was only practice for this. Castiel’s eyes kept flicking between Dean’s lovely cock and his lovelier face, where his bottom lip was caught between his teeth. 

“What do you want, Castiel?” Dean asked, voice low and gruff like the lust hanging over the two of them was as stifling as it felt. Castiel’s breath hitched at the use of his full name. 

He worked his jaw for a second. He couldn't remember the last time a client had made him this breathless. He wondered when it would stop surprising him with Dean. “Wanna suck your cock.” 

Dean grinned crookedly. He leaned forward and reached a hand around the back of Castiel’s head, immediately burying his fingers and smoothing up his scalp. Castiel felt tingles erupt in the path Dean’s hand left. He pulled Castiel in for a kiss, his tongue flicking out to flirt with Castiel’s bottom lip. He leaned back, leaving Castiel’s eyes to flutter for a second. Dean’s hand pulled his face towards Dean’s erection, the tip pearly with wetness. Castiel licked his lips, trying to work some moisture back into his suddenly-dry mouth. 

Dean’s hand stopped Castiel’s movement right before his lips could make contact with Dean’s cock. Castiel heard himself whine, and looked up at Dean with what he hoped was a pleading expression. He couldn’t take much more of this waiting; he wanted Dean’s cock now. 

“Yeah, you want it real bad, don’t you baby?” Dean had the audacity to look smug right now. His fingers tightened a bit in Castiel’s hair and Castiel felt his cock throb in his too-tight pants. “You’d do it too. You’d sit on the floor of my garage and you’d suck my cock right here, wouldn’t you?” Castiel nodded furiously. Dean brought him just the tiniest bit closer. Castiel tried to get his mouth around Dean, but was restrained. He resigned himself to pressing hot kisses to wherever he could reach. Dean sighed and petted through Castiel’s hair with his free hand. “God, you look so good like this, so eager.” He sounded out of breath. Castiel was just trying to touch as much skin as he could. He crept his hands up Dean’s legs and planted them on his knees, emboldened when Dean didn’t stop him. 

“Please—please let me suck your cock… sir.” Castiel tacked on at the end, in a fit of desperation. 

That got Dean’s attention. He sat back, hand still firmly in place. “I think I actually want you up here in my lap.” Castiel hesitated, but when Dean raised an eyebrow, he hurried to comply. Dean’s hands went to his hips to balance him, stroking over the skin right above the waistband of his jeans. Castiel hoped that he’d be asked to take them off soon enough. “Yeah, this is better. I can kiss you better up here,” he captured Castiel’s mouth as if to prove that point, “but there’s something I want to try.” 

“Yes, sir. Yes. I want it.” 

Dean smirked. “You don’t even know what it is yet, baby.” 

Castiel swallowed, trying to control himself. He didn’t want to look too eager and risk Dean thinking he was too forceful to be a sub. 

The older man leaned in close to Castiel’s ear and whispered, “I want to open you up with my fingers.” He laved his tongue over Castiel’s ear and down his neck. Castiel’s entire body shuddered. “And then I want to fuck you.” 

A whine tore out of Castiel’s throat and he pressed himself as close to Dean as he could. There was so much heat in his body, he could almost forget the pang of unease that went through him at Dean’s words. He wanted the man in front of him so badly, how could he ever deny him this? 

From there, it was quick work getting Castiel out of his pants and onto his front on the couch. Dean crouched behind him, one foot on the floor to balance himself, and the other tucked up underneath. He had produced lube from somewhere Castiel couldn't bring himself to care about and was now running his hands over Castiel’s ass. Even in his wildest masturbatory fantasies, he had never gotten so far as to stick a finger or anything up his own ass. Clients sometimes liked to offer to do it to him, but he had never taken them up on it. 

Castiel didn’t know why, but he expected Dean to move a bit faster than the glacial pace he had chosen. He took a dry finger and just rubbed over Castiel’s hole. It felt a bit strange, but Castiel decided he liked it. Dean pressed a kiss to each of the dimples in Castiel’s spine, which made him smile. 

“I’m gonna slick up my finger now.” Dean sounded as out of breath as Castiel felt. Dean took his fingers away and Castiel heard the pop of the lid on the lube. Dean’s touch was back now, cooler than before. He circled around Castiel’s hole before gently—ever so gently—pushing his index finger inside. 

Castiel had to catch his breath. Dean was inside him. There was a finger inside him and it was circling. Sparks raced up and down Castiel’s spine and went straight to his cock. He couldn't believe he hadn’t done this before. He vaguely heard Dean murmuring encouragement to him, but he was too caught up in his own head to pick out what was being said. 

The finger vanished and reappeared, slicker this time. Castiel wondered when Dean would add another finger. And then another. And then his cock perhaps. Would he tell Castiel when he was ready? What if he wasn’t stretched enough? Castiel felt his breath catch when Dean started thrusting lightly into him, but he couldn't find the same pleasure in the act that he had. He screwed his eyes shut and thrust back onto Dean’s fingers, gasping when a particularly hard jab caught his insides uncomfortably. He could do this. He could totally do this. People did it all the time, especially sex workers. What if he wasn’t any good at this? Would Dean throw him out? Gabriel’s words started low in the back of his head again. He was right, Castiel was there for one purpose only, to make Dean feel good. And Castiel would do anything for Dean. He couldn't hear Dean whispering to him anymore, it was drowned out by the rushing sound in his ears. He became aware that he wasn’t hard anymore and he redoubled his focus, trying to just feel Dean’s hands on him, soothing. But no, the hands were restricting. Pulling. Shoving. Castiel grit his teeth and tried to find that pleasure again. 

He wasn’t aware he was shaking until Dean’s voice finally broke through. 

“—stiel! Jesus, come on baby…” Dean sounded far away. And worried. 

Castiel looked around. He was curled in on himself on his side. He hadn’t been aware of doing that. He also wasn’t aware of the tears still making tracks down his cheeks. 

Dean was in front of him, giving him plenty of space, but with a hand stretched out if he needed to intervene. His expression looked pinched. 

Fuck, Castiel had let him down. He had tried to act like an adult, but he failed. 

Castiel scrambled upwards to a sitting position. Dean had pulled his pants back up, and Castiel noticed with a sinking heart that he was no longer hard. He reached for Dean’s zipper, only to have it knocked away, albeit gently, by Dean, who made a forbidding noise. 

"Why won't you let me touch you?" Castiel asked, and hated how close his voice sounded to breaking again. 

Dean’s hand came up to wipe Castiel’s cheek.

“Are you kidding me—alright, hang on,” Dean straightened up and walked over to the fridge. Castiel craned his neck around to make sure he wasn’t going anywhere, but he only pulled a bottle of water out of the fridge and returned to sit next to Castiel, still giving him plenty of room. He reached down and handed Castiel’s pants to him, with the silent order to put them on that Castiel didn’t dare ignore. When he was dressed, he immediately scooted closer to Dean, who sighed and put his arm gingerly around Castiel’s shoulders. 

Neither of them spoke for a while. 

“You’re supposed to safeword if it gets to be too much.” Dean’s tone sounded flat and he wouldn’t look at Castiel. 

Castiel swiped at his cheeks again, hoping he was being sneaky about it. “I’m sorry. It won’t happen again. I’ll try harder next time.” 

He chanced a glance up at Dean to see his expression. Dean was shaking his head and had his lips curled in a grimace. “That’s not—you don't have to try harder, Cas. That’s not… that’s not what I’m mad about.” 

Castiel shrunk back into himself and pulled his body out from underneath Dean’s. “Do you want me to go?” 

Dean looked over and raised an eyebrow at him. Where it had been fun and sexy before, Castiel now felt like he was being punished like a rowdy schoolboy. “Do you want to leave?” 

“Not really, if I’m being honest. I can be good—“

“Dammit Cas,” Dean stood up suddenly and walked a few steps forward, hands on his hips and not facing Castiel, “It’s not about being good or giving me what I want…” he turned and faced Castiel. “I told you when we made the deal in the first place, I’m not interested in what you think I want! I’m trusting you to tell when it’s too much. Even if it’s just at a kiss, and especially if it’s before sex. That’s how this works. That’s how this—“ he gestured angrily between the two of them, “—this relationship has to work!” Dean turned away again, hand on his mouth. 

Castiel didn’t know what to say. He settled on the truth. “I want you,” he starts. Dean snorts in derision. Castiel closed his eyes, "I feel like a kid. Like I'm just struggling to balance out this relationship a bit, but... I _can't._ There's this... mental block and--" 

"That sounds like you don't really want to be with me." When Dean said it, the words didn't sound like he was trying to make Castiel feel guilty, but almost self-depreciatory. He blamed himself. 

Castiel grabbed Dean's hand and pressed his lips to his knuckles. The skin tasted faintly of lube and how the engine oil smelled. "How can you think that? You've made me come spectacularly at least twice a day since I've been here. Maybe more when I'm really lucky. I want you. I promise, that’s not a lie. I want to be with you so much that it aches. But, I can’t—I’m not…” he trailed off, lost. He couldn't say too much. _Do the job, do the job, do the job._

Dean sighs. “Your brain is still telling you something else?” 

“Yes. That.” 

Dean ran his hand through his hair, ruffling it. “You have to know, I’m not mad at you for wanting to quit before we got to the main event. Okay?” He turned back and walked over to the couch, sitting close to Castiel. “I mean it. I’m not mad about that. But I need to be able to trust you to safeword if it gets to be too much. Otherwise, I’m gonna be in constant fear that I’m overwhelming you and that… don’t make me do that, Cas.” His eyes were pleading with Castiel to understand. 

“Okay.” Castiel meant it with every cell in his body. “I promise Dean. I’ll tell you.” 

Dean smiled, but it was pained. “Okay. I think if it’s alright with you, I’m gonna work down here a bit more before dinner. You gonna go upstairs or do you wanna hang out with me some more?” 

Castiel stood up and turned around, automatically fitting himself between Dean’s knees. Dean’s hands smoothed up his thighs and settled on his waist. Even if Castiel couldn't commit to this whole sex thing all the way, he still loved the way Dean’s hands felt on him, strong and warm. 

“I could probably stand to work on my painting some more. Just don’t blast your music so loud this time. And stop dancing around, you’re very distracting.” 

Dean rested his head against Castiel’s stomach and he snickered. Castiel raked his hands through Dean’s hair, making it stand on end. Dean looked up through his lashes, “Deal.”

**Notes for the Chapter:**

> For the person that wanted "sweaty, greasy, garage sex", I'm so sorry about the cop out. It's coming, I promise... 
> 
> As for the rest of you, I am so _SO_ sorry this was not out earlier. School is kicking into high gear, so deadlines are looming about as high as I can see. I hope to be better about updates, but they will probably be aimed more towards Wednesdays now, rather than Sundays. 
> 
> As always, I thank you all so whole-heartedly for reading. When I started this piece, it was only about four chapters, and I thought maybe fifteen people would read it. I am astounded by the amount of comments this has gotten, and I love each and every one of them. Thank you for sticking with it, my friends. It is truly a privilege to see this story through to the end. 
> 
> -azo
> 
> P.S. - connect with me on tumblr! Search for azo-dye!


	10. Blue on Black

**Summary for the Chapter:**

> They gotta get out of that garage, nothing productive happens there...

The tension from the garage seemed to set low on Castiel’s mind the next week. He tried to be so good for Dean, being extra attentive when he got home from meetings, offering to wash him off nice and slow in the shower, and volunteering to keep him company while he went looking for a specific part for his car one sunny Sunday afternoon. That day had been well-spent, making out lazily in the back of Dean’s car on the side of the road twenty minutes outside the city’s north limit. Dean seemed to enjoy the time spent with him, but didn’t try to initiate anything too serious. Nothing that could involve using a safeword.

Nothing that Castiel could mess up by not using his safeword. 

Although Castiel was the one being paid, he couldn’t help but feel a bit cheated out of something wonderful whenever Dean would bat his hands away from his zipper and carry on kissing him like he wanted nothing else in the world. Castiel wondered if maybe Dean had lost interest in being with him in that way, if he thought of Castiel as a child who couldn't be trusted to make serious choices. He voiced these concerns to Dean sometimes, petulant, but wanting to communicate his problems, but was gently pushed aside. 

“If you think that I think you’re a child, we’re a kinkier pair than I thought,” he would say, laughing. 

Castiel smiled, but still felt the frustration. How would he ever get past this mental block if he was never given the chance? 

Still, even with this frustration, they carried on with their routine. He averaged about five nights at Dean’s place, four or more in Dean’s bed with him, and the rest at his own apartment with Anna. Castiel hated those nights the worst, but understood that Dean sometimes had early morning meetings or had to leave town. Sometimes, too, Castiel had to take some distance from Dean when the bookstore started getting steadily busier with the upcoming fall semester. Classes at the Institute started approximately a week after Loyola and U of Chi, and students were starting to stream back into the already bursting city. Still, between the worried freshmen, and the even more worried parents, Castiel found solace in between the towering stacks of shelves at the back of the quiet bookstore. It was a good place to think about… anything.

Turning Pages was tucked in one of the quietest streets of Old Town, not more than three blocks from the Institute. The owner, a more than ancient Hispanic man with leather-brown skin and a thick white mustache spoke with a steady, but whisper-quiet voice, as he directed his patrons to the newest anthology of Tennyson poetry, or a section of artist biographies. Sr. Guerrero came to Chicago from a small village just south of Mexico City when he was in his early forties. He’d had a wife, Isabel, and his baby girl, Carmen. Isabel had been fluent in English, Sr. Guerrero had not. On quiet days, Sr. Guerrero liked to tell Castiel about his village and his wife’s cooking. Castiel had never had the chance to eat truly authentic Mexican cuisine, like his boss described, but he imagined he could tell a stranger everything about how Isabel made the sopapillas on Christmas morning. Sadly, Sr. Guerrero had lost his wife during an immigration raid gone wrong back in the nineties. Carmen had since grown up and gone to university. “The prettiest civil engineer there ever was,” Sr. Guerrero said of her, hopelessly fond of his only daughter. Now retired from his job as a bank teller, he owned one of the best small bookstores in the area. They carried everything from Pablo Neruda to Shel Silverstein in poetry, and from Dickens to Rowling in fiction. It was only happenstance that Castiel got his job at all. Sr. Guerrero, good as he was at helping people find new stories to love, was getting on in years and needed help with stocking, pricing, and other odd jobs around the store. Castiel happened to wander in out of the rain one day, freshly homeless after another year at the Institute, and Sr. Guerrero liked the look of him and hired him on the spot. Castiel didn’t work much, just a few hours a week between classes and… other side work. Sr. Guerrero was always glad to see him. 

Castiel liked Sr. Guerrero enough, that he sometimes stopped in to say hello, even when he wasn’t working, such as now, while Dean was at a meeting with his design team. He had told Castiel that morning that the meeting shouldn’t be more than a few hours, that he planned on telling the design team to just go with blue and stop the all-out feud that was tearing their department apart. That had been at nine this morning, and this was now three in the afternoon. Castiel imagined that there would be a story about a hilariously dysfunctional work team when he saw Dean again. 

Sr. Guerrero’s latest and greatest hobby was telling Castiel he didn’t eat enough with a wide smile and a teasing wink. Castiel expected the same when he walked into the store, tsking at the small blue-gray cat, Anita, who tried to paw her way up into his arms immediately upon entry. Instead, as he brought a purring Anita to the counter and set her down, Sr. Guerrero took one look at him, and said “I see that your woman is giving you troubles.” 

Castiel blinked. “Um.” He said, intelligently. 

Sr. Guerrero scooped his cat off the counter and deposited her on the stairs that ran behind the counter up to the tiny apartment Sr. Guerrero lived in above the shop. He turned back to Castiel and chuckled. “No young man comes into this shop looking as troubled as you are, Castiel.” 

“I’m always troubled.” 

“This is a different face of troubled, then, isn’t it?” 

Castiel frowned. “I haven’t got a woman.” 

Sr. Guerrero rolled his eyes, “Then your genderless-friend-of-significance is giving you a headache, _Dios mio…_ ” he said in his thick accent. 

Castiel had to smile. Never let it be said that Sr. Guerrero was not the second most awesome boss Castiel had ever had. 

Still, it wasn’t like he could exactly drop his current problem in Sr. Guerrero’s lap without some heavy explanation and extreme awkwardness. “It’s… complicated, I guess.” 

Sr. Guerrero hmm’d in acknowledgement. “And does this genderless friend know they are being complicated?” He pushed a silver pair of spectacles up his nose and turned back to his calculator, where he was calculating shipping costs by hand. 

“I think I’m the one being complicated, actually.” Castiel stroked underneath Anita’s chin when she leapt lightly back onto the desk from the stairs, batting first at Sr. Guerrero’s pen, but nudging at Castiel’s stomach for some attention when her owner gently poked her tummy with the pen. 

Sr. Guerrero waved a hand. “It is because you are an artist, Castiel. You are all the same.” He looked up with a teasing smile. Castiel rolled his eyes and looked away. 

“Yeah, can’t trust us with anything.” 

“I’m sure your friend appreciates how complicated you think you are. Otherwise…” he looked up at Castiel, “I will kill him.” 

Castiel blinked again. “I… didn’t say it was a ‘him’ either.” 

A full three seconds passed, before Sr. Guerrero’s face split into a laugh. “Castiel, this is worse than I thought. You are so serious because of this boy!” 

Castiel sighed. “I still didn’t say he was a boy.” 

Sr. Guerrero winked and tapped his temple with his blue pen. “I raised a teenager. I know everything.” 

Castiel huffed and rolled his eyes again, scooping up Anita to take with him to the front. He knew Sr. Guerrero had just gotten in a set of really nice coffee table books on different Expressionist artists. He couldn’t afford them by any means, but he wanted to look at them all the same. He stopped, thinking of the stack of cash in his wallet now. Maybe he could afford them now.

Huh. 

Anita was set down in her basket near the door while he paged through the Jackson Pollack book. The images were incredible, taking up full spreads in the book with detailed descriptions of Pollack’s process and inspiration beside each one. From a technical standpoint, Castiel hated Pollack to pieces. Who did he think he was, just dripping paint of a canvas on the dirty floor of his garage and calling it art? What was the point? But from an artistic viewpoint, Castiel appreciated the man’s ingenuity. He hated it when people looked at a piece of work and said, “I could do that,” as if comparing the artist’s skill to that of a civilian could take the arts off their finely crafted pedestal. Yes, anyone could paint, but true genius came from being the first one to put it on canvas and call it art. He scoffed at a critic’s review of Pollack’s exhibit in New York as it was printed next to _Convergence_. 

“The basic values of a composition are lost in a clutter of more or less meaningless embellishment… - Robert Coates” 

Meaningless embellishment was practically the core foundation of art. How could you see the basic composition without the embellishment? It was as part of the original composition as the signature at the bottom. You couldn’t just pick parts of a piece of art, of anything really, that you didn’t like and just forget about them because it was more convenient that way. They were still there, always there. Meaningless embellishments, unfavorable traits, bad habits. They were hard to get away from. Art without the embellishment wound up as big plain blocks of color on a plain canvas. Okay, anyone _could_ paint, but that didn’t mean everyone _should…_

“I bet Coates was a Rothko fanboy.” He said aloud, mostly to Anita. The little cat yawned and lay her head back down, flicking her fluffy tail over the side of the basket. 

“Are you talking to yourself again, Castiel?” Sr. Guerrero said from the desk, quiet voice carrying over the various creaks of the shop, smile evident in his voice. 

“How can they call Pollack’s work meaningless embellishment?” 

“Sometimes those on the outside cannot understand what they are looking at, I suppose.” Sr. Guerrero said, sagely. “But what does Pollack care? He likes his paint splatters just fine.”

Castiel looked back at _Convergence_. “Amen,” he said, closing the book. 

…

“Missed you today.” Dean said randomly over a half-empty pizza box on the coffee table of the garage. 

Castiel took a swig of beer and glanced back, paintbrush tucked over one ear. “I missed you too. How was your meeting?” 

They hadn’t said much when Dean had gotten back that afternoon, practically evening. They’d made out on the couch for about forty minutes, before Dean popped his head up, stomach growling. He’d grumbled about needing pizza and pulled a laughing Castiel up off the couch. They’d taken their pizza and a six pack down to the garage. It was where they spent most of their free time now. Castiel was glad to have settled into a routine, even more glad that the routine involved painting. 

“It was fine, I guess. Damn bastards can’t figure out why the project’s so delayed and they’re still running around yelling about navy versus royal blue. Who the fuck cares?” Dean tossed his greasy rag over his work bench and snagged his own beer, taking a pull. 

Castiel set down his beer and grabbed the paintbrush behind his ear. “Oh, probably some snooty art person who thinks about colors all the fuckin’ time. What losers…” he said dryly, grabbing his mixing palette and palette knife. He was turned away from Dean, but he could practically hear the color rising in Dean’s cheeks. 

“That’s… not what I meant.” 

Castiel chuckled, reaching for a tube of portrait pink. He was just getting started on the colors for his painting, and wanted to get the base coat down for the eyelid and skin surrounding the eye. He still didn’t have a plan for the iris, but wanted to get the rest of the painting planned out before he committed to anything. “Well, are you looking for more of a professional tone or a friendly one?” 

“I dunno, it’s for an insurance initiative. Affordable insurance that covers everything, ya know?” 

“So, something relatable to a lot of people?” 

“Guess so.” Dean sauntered closer, wrapping an arm around Castiel’s hips and peering over his shoulder while he mixed paint. 

Castiel added a hint of ochre, bringing the color to a neutral peach. “What does the design team say?” With his palette knife, he scooped the whole mess and smeared it around while he mixed, using the tip to swirl the colors together. “Hand me that white please?” 

Dean reached for the tube of Titanium White, but faltered when he noticed the half empty tube of Cool White. Castiel chuckled as he visibly waffled between the two tubes. Painting with Dean was fun, and Castiel wasn’t about to give up on the show. Finally, Dean settled on the Titanium, handing it to Castiel with a faux casualness. Castiel tried to hold back a smile. 

Dean huffed. “Don’t look at me like that, I don’t know paint like you,” he said, standing up a few tubes of paint that had fallen over. “The designers just say that the blue we pick will ‘define the brand’ or whatever. That seems like a lot of pressure on a single color.” 

Castiel spread in an amount of white to his mix, and wiped the palette knife on the edge of the palette to clean it off. With the barest edge, he dipped into the magenta. Beside him, Dean said, “Why do you have that tiny little bit of pink? That isn’t going to—“ Castiel started mixing. “I—oh.” Dean said, as the shade gained warmth and depth. “That wasn’t the color I expected.” 

“You should watch some of those paint mixing videos on YouTube. You’d have a lot of fun.” Castiel nudged Dean. 

“I watched one that said it was supposed to do something weird to your brain, like… as-mer? I dunno.” 

Scraping off the palette knife again, Castiel turned back to his brushes, pulling out a wide flat bright. “I think that people would be more comfortable with a nice navy for the logo. It’s familiar and sturdy.” 

Dean scoffed. “How can a color be sturdy?” 

“Soothing, then.” 

“This is like that one time you tried to tell me that that one Zeppelin song sounded ‘aubergine’… it’s just colors to me.” Dean chuckled and pressed a kiss to Castiel’s temple. He walked back over to his work bench. “Navy sounds good, though.” 

The two lapsed back into silence as they worked. Dean kept the radio at an acceptable volume and refrained from dancing around too much as he worked, as per Castiel’s request to actually get work done. 

Castiel wasn’t quite sure what Dean was doing over there this time, however. It seemed that he was always working on a new project, either for himself or a friend. Castiel thought that perhaps in another life, Dean could have made a living from restoring old cars and fixing broken ones. Whatever Dean was working on today, it was mostly covered by a sheet. Dean didn’t offer to show Castiel, and Castiel didn’t pry… too much.

There was something enticing about a secret. 

“Sure you still can’t tell me what you’ve got under that sheet?” Castiel tried to appear casual as he put down his base coat of flesh-tone paint. 

“Sure I still can’t get you under my sheets?” Dean replied in the same tone, eyes sparkling from across the garage. 

“Maybe we can work out a quid pro quo?” 

Dean snorted. “You show me yours, I’ll show you mine?” 

“All you’ve gotta do is say the word, and I’m yours.” Castiel was mostly teasing, flirting coming as naturally as breathing with Dean. Not that he didn’t fully want to be with this man, under this man, on top of, etc. etc. 

“It’s a surprise.” Dean said, still smiling. 

“I can keep a secret.” 

“Not from yourself, you can’t. Work on your painting.” 

“So it’s a gift then, is it?” Castiel put his brush down and pulled out a smaller detail brush to get up close to the lines. 

“Yep. Those are in the contract, you know. That you signed.” 

“I’m just saying… I’m making you a gift and you already know what it is.” 

“That’s decidedly not in the contract.” 

Castiel huffed. “Oh, come on.” 

“Your presence is a present, Cas. Can’t ask for more than that. I, however, am allowed to offer you a yacht if I want to.” 

Castiel grumbled to himself, “That doesn’t mean I’d take it.” 

“I heard that, mister. You better hope I don’t get you a yacht.” 

“As long as you come with me.” Castiel was really laying it on thick, but Dean was fun. Flirting was fun with him. 

Dean chuckled. “We’d have fun on a yacht, I think. Just us, and the water, and the sun. No one else around.” 

“Scenic.” Castiel agreed. 

“Just you and me, and maybe a bottle of champagne. I bet you’re a riot when you’re drunk.” 

“I have quite a high tolerance for alcohol. I did go to a public high school.” 

“Still,” Dean continued, his tone different. “Bet you’d be a pretty handsy drunk.” 

“You’d like that.” 

“Would you wear board shorts, or are you a speedo kinda guy?” Dean leaned up against his work bench now, not even pretending to work.” 

“Depends on the occasion.” Castiel put down his brush, coming around the easel to lean against his own bench. They were several feet apart, but the heat in the room was slowly kicking up a few notches. 

“See, I have this theory.” Dean crossed his arms, smirk on his face. “People only play strip poker when they’re drunk, right? And I bet you’d love to play strip poker.” 

“And why would you think that?” Castiel was well aware of how quickly this moment could be ruined if Dean said something like ‘because you’re a hooker.’ 

“Because I’d ask you to.” Dean had a lecherous look on his face that was instantly transformed by the soft, genuine tone to his voice, like he hadn’t meant to say it that way. 

Oh, but Castiel was in trouble. 

“You’d ask me to strip for you?” Castiel took a few steps forward, slow as he liked. He toed off his shoes and socks along the way, so he was left barefoot a foot from where Dean stood. He reached around Dean, delighting in the way Dean seemed to tense up in anticipation. He grabbed Dean’s phone as it was streaming to the stereo. Flicking through a few playlists, he picked out a Black Keys song he was pretty convinced Dean didn’t even know he had. The slow, sultry beat started and he stepped back an inch, tucking the phone into Dean’s front pocket, grabbing himself a generous handful of Dean’s junk on the way. Yeah, Dean was already into this. 

He slowly swayed his hips in rhythm with the music, not going too fast, but keeping it pretty natural. He stayed close to Dean, no more than a hand’s reach away. He pulled his shirt off slowly, revealing his stomach inch by inch. Dean kept his eyes glued to the skin as it was revealed. Castiel tugged the shirt over his chest, thumbing his own nipples along the way. He made a sound, causing Dean to answer with a small whimper of his own at the sight. Ruffling his hair as he pulled it all the way off, he dropped the shirt behind himself, kicking it away so he couldn't slip on it, accidentally. That would kinda ruin the moment. 

His fingers found the hem of Dean’s shirt, stroking softly over his skin as he pulled upwards. Dean’s gaze was locked on his and he didn’t dare look away. “I’d only strip if I could get you naked too. Do you think that’d be amenable?” 

Dean nodded, dazed. His hands reached down to help Castiel pull the shirt all the way off. He tossed it to land somewhere near Castiel’s on the floor. Castiel grabbed Dean’s hands and pushed them down to cup his ass. He undid the zipper of his own jeans and tugged at the flaps enough to get his erection, still in his boxers, front and center, impossible to miss. Sure enough, Dean seemed to have a hard time keeping his breathing in check. When Castiel leaned into his body, grinding against him, Dean’s hands took big handfuls of his ass, pushing him forward even more. Castiel carefully kept his mouth out of the way of Dean’s just yet, even though Dean kept reaching forward for him. 

Instead, Dean settled for resting his forehead on Castiel’s. “God, this is like an upright lap dance.” Castiel could feel how much this was doing it for Dean, the evidence was hot and hard against his hip. He grinned against Dean’s cheek. 

Castiel trailed his hands up Dean’s chest. White and yellow paint covered his skin in swipes where he wasn’t very careful with his brush. Coming up around Dean’s neck, Castiel noticed that Dean had streaks of engine oil on his skin as well. Covered in mess, here they both were, grinding up against each other in the garage. He tilted Dean’s head up, and suckered a hard kiss to his neck, causing Dean’s breath to hitch beautifully. Dean’s hands grabbed him harder and rolled his hips slow. 

“Cas—‘f you’re not careful, Imma pick you up and throw you over the hood of my baby.” 

Well, if that thought didn’t cause something hot to curl in Castiel’s stomach. He tongued across Dean’s clavicle. “Do it,” he whispered heatedly against Dean’s skin. 

With a growl, Dean dropped and scooped him up by the knees, putting him a few inches above Dean. Twisting his fingers in light brown hair, he pulled Dean’s mouth to kiss as Dean walked them a few feet to the left where the black Impala Dean loved so much was parked. He squeezed Castiel’s thighs, telling him to hang on, while he pulled Castiel’s pants off. Left in his boxers, he was deposited onto the hood of the Impala, while Dean made room for himself between Castiel’s legs. Slowly, Dean ran his fingers up the length of Castiel’s cock, causing little bolts of lightning to spark at the contact. 

“This feels like a chick position.” Castiel huffed, fighting a shiver. 

“I dunno, Cas,” Dean said between kisses. “You keep gettin’ so wet for me. I’ve had girls who didn’t get this riled up when I spent hours playin’ with their clit.” 

Castiel didn’t particularly like the thought of a girl, or anyone, making Dean feel like he couldn't shake apart anyone’s world with minimal effort. “I would,” he said, breathless. “If I had a clit and you were touching me like this, I’d never let you leave this position.” 

“Fuck,” Dean hid his face in Castiel’s neck for a second. “You are kinkier than I thought.” He returned to Castiel’s lips. 

Castiel reached down to pull Dean’s jeans down below his ass, so they could grind together without as much fabric in the way. As soon as he was relatively free, Dean pulled them forwards and just laid into Castiel, pushing his erection against Castiel’s. His eyes were so bright and wild-looking. When Castiel leaned back a bit, holding himself up with his hand, Dean followed, the new angle pulling sounds out of both of them. 

“God, you drive me crazy. I never last as long as I want to.” Castiel panted against Dean’s mouth. 

“Don’t say that like it’s a bad thing, sweetheart. I love turnin’ you on. Best part of my day.” 

“Even with design meetings?” Castiel swiveled his hips, causing Dean to nearly lose support in his arms. 

“Fuuuuuuck. Come ‘ere.” Dean attacked his mouth with new fervor. 

Castiel could tell that Dean was getting close, because his thrusts were getting faster and shallower. “Gonna come for me?” He egged Dean on. “Gonna come in your underwear? Yeah, you’re so close, aren’t you? Want me to come with you? Make a mess all over your pretty car?” 

Dean whined and thrust a final time, pushing in close and spilling inside his boxers, a dampness Castiel could feel on his own skin. He bit down on Castiel’s nipple, causing Castiel’s arms to give out and his back to hit the hood while his cock spurted in resounding agreement. 

Face hidden in Castiel’s neck, Dean’s voice was muffled. “Why does that turn me on when you say you’re gonna come all over my car?” 

Castiel’s hand slapped him lightly on the back. Dean’s skin was sweaty and he was sure his own wasn’t much better. “Because you’re a raging slut, just like I am?” 

Dean hummed in agreement. After a while, he leaned back and took hold of Castiel’s thighs again. He lifted Castiel off the car and took them back to the sectional that had almost been the spot of their first time. Dean sat down and held Castiel in his lap. Their come was cooling in their boxers and they were both still covered in sweat and evidence of their hobbies, but neither of them cared. 

“So that’s a no? You won’t show me what’s under the sheet?” Castiel couldn’t help but ask. 

Dean chuckled but shook his head. After a while, he said, “Anyone ever told you before how easy you are to read?”

Castiel hesitated but said no. 

“Good,” Dean said, nodding and leaning his head against the back of the couch, closing his eyes. “Because you might try to hide those pretty faces from me if you knew.” 

Castiel heaved a laugh and ran a hand through Dean’s sweaty hair, leaning back into Dean’s warmth. He shivered when Dean’s arms tightened around him. 

Oh yeah, Castiel was in big trouble.

**Notes for the Chapter:**

> ... yeah, let's just be real here. I'm on no one's update schedule anymore. That's okay, I have a chapter here and that's all that matters, right? I fear no one. 
> 
> Hope you enjoy this chapter! 
> 
> -azo
> 
> Connect with me on Tumblr! Search for azo_dye!!!


	11. You Can't Always Get What You Want

**Summary for the Chapter:**

> Cas has a bad day.

Castiel was in a bad way. He hadn’t slept well last night, he was at the apartment because Dean had been on a business trip the last three days, he’d had a line of rude customers at the bookstore all looking for some new pseudo-medicinal healer lady’s latest title—seriously, _white women_ —and to top it all off, he’d had a meeting with his advisor at the Institute, and it… hadn’t gone well. 

…

“No, tuition isn’t going to be a problem.” He’d said, leaning back in his chair. He’d never liked his advisor, the man too smug and condescending for Castiel’s liking. Balthazar Reynolds, and what the fuck kind of name was that, had tufty blond hair and wore v-neck shirts under his blazer that were on the wrong side of “too low for comfort.” 

Balthazar had steepled his fingers and smiled pityingly at Castiel over the mahogany desk that was clearly too large for the tiny office encompassing it. “That’s all fine and good, Mr. Novak, but you have a—a history, shall we say, of cutting it rather close to meeting deadlines with the financial aid department.” He leaned back in his oxblood leather office chair. “We’re just concerned that it will be too much for you with this extra coursework.” 

“So, you think I should what… drop out?” 

Balthazar had smiled, rather smugly in Castiel’s opinion, down at his desk. “If you think that’s necessary, you should consider your options. You could also push a few of these classes off until next year. Don’t want you to get… overwhelmed with your financial situation.” 

“My financial situation…” Castiel had repeated, arching an eyebrow. 

Balthazar’s face had changed into that of a concern that Castiel didn’t buy for a second. “No parental support, living off campus, and the W2 forms from that little bookstore you turned in last year. What we’re saying, Cather—“

“Castiel.” 

“—is that we’re just worried—“ 

“My situation is under control and I need to take those classes so I can graduate,” Castiel had said with gritted teeth. “I don’t want to be here for another whole year. I don’t have time for that.” 

“Maybe if you took out another loan—“ 

“I can’t.” 

“There’s always work study—“

“I don’t need it! I have the money—!” 

Balthazar had sighed, clearly growing impatient and losing his mask of cool. “Saying you have the money isn’t going to convince the financial aid department, Castle—“

“— _Castiel_ —“ 

“—and they’ve included a note on your registration for this year. If the entire amount for the year isn’t paid up front, I can’t enroll you for this semester.” He finished and looked at Castiel expectantly. A long moment passed between them. 

“Fine. Easy.” 

“I’m just saying, there are ways around this, Cas—Mr. Novak. Don’t strain yourself.” 

“Two weeks. I’ll have the whole amount by then.” Easy enough in theory. He could just ask Dean for the amount. He bet that Dean would pay it no problem. That wasn’t really the issue here, however. 

Balthazar had blinked and shuffled through a stack of papers, picking one with a series of red marks on it. “… you’re going to have the thirty-thousand amount in two weeks? Mr. Novak, our records show that last year, you struggled to make the minimum payment on your plan eight months out of the nine—“ 

“Last year was different. Two weeks.” 

Balthazar had set the paper down. “Well, I… certainly hope you can meet the two week deadline, Mr. Novak. We wouldn’t want to bar you from entering this institution.” 

“Yeah. See you in two weeks, Bartholomew.” Castiel had turned to leave, his vision tinged red with his anger. 

Behind him, Balthazar had chuckled. “It’s actually Balth—“ Castiel had shut the door with finality. He hoped the force had knocked over one of the pretentious looking medals on the wall. 

…

Presently, Castiel stood in front of a blank canvas. The eye outline was sat safely under a cloth a few feet away, leaned up against the wall of the garage. The canvas in front of him was about to get wrecked. 

Walking back to pluck a tube of bright yellow off his work table, Castiel held the color in his hand for a second, looking for his palette. It wasn’t where he remembered leaving it, near the shop sink, and it wasn’t with his other tools in his big art case. He turned the tube over a few times. Glancing back up at the canvas, he shrugged and popped the lid. He squeezed out a bit of the yellow and stepped back up to his palette. If his palette wanted to go missing, fine. He didn’t need it. Angrily, he whipped his wrist, splattering the paint across the canvas diagonally in a blot pattern not unlike a Rorschach ink test panel. 

Oh, he liked the look of that. So wild and unexpected, completely unlike his normal neat brushstrokes of color, defining a space with line and space. At the same time, he hated it. Hated that there was now paint on the floor. He scooped up some more paint on his index and middle fingers. Better make the mess worth it, then. He smeared the yellow over top of the splatters, smearing some to the very edge of the canvas and dripping down onto the drop cloth. 

Blue, he needed blue. He spun around, going back towards his work bench, tossing the yellow back down. He swept a half-empty tube of Mars Black onto the floor, followed quickly by a sample-sized tube of a shocking shade of violet. He swore and fumbled with the cap on the ultramarine, stalking to the canvas again. 

A little bit of this could deepen any color into a stunning shade of indigo. What could an entire stripe of it do? 

Castiel was making a mess. He knew it, and he didn’t care. He didn’t care about how he was basically wasting a canvas, didn’t care that he was using up his paints, didn’t even care about the floor or the drop cloth, which was steadily becoming more of a mess than the canvas. What did he care? Maybe if he sold it, he could afford the tuition for his stupid art college on his own, without the help of his sugar daddy to foot the bill.

God, why was he such a screw-up? He liked art, knew he was good at it, but why did he pick an institution where they so clearly cared more about his money than his ability? The way Balthazar talked—Castiel cleared his throat to push back the tears forming—made it sound like the entire staff at the Institute was against him. If he couldn't pay the thirty thousand in two weeks, he couldn't enroll. Or he’d have to take a lighter schedule. 

He’d been there for three years already, though. Most of the people in his program when he’d started had graduated already, able to pay for the intensive schedule the Institute required. 

And it didn’t have to be a problem. Dean could pay for the entire tuition. He’d dropped several hundred dollars at the art store without batting an eye, even called the salary that he paid Castiel “pocket change.” If Castiel asked, there was no doubt in his mind that Dean would pay the tuition and shut up Balthazar and the rest of the financial aid department. But that wasn’t the real reason Castiel was pissed. He hated that this whole arrangement was so fucking necessary for Castiel’s survival. He didn’t like being so dependent on Dean, either for money or this weird pull Castiel felt to be near the man. He hated how much he needed the paycheck from Dean to live out what he wanted to do. Sure, it wasn’t strictly necessary to graduate from the Institute, but having a degree that told the world he was at least qualified to draw and paint opened a hell of a lot more doors than a freelancer with an inch-thick sketchbook, knocking on the door of every design firm in the city. 

It didn’t even necessarily have to be Dean’s money paying the bill, either. Now that he had a better handle on this whole sugar daddy arrangement, there was little stopping him from finding two or three other sugar daddies to pay his way through school. 

Castiel stepped back from his canvas. He needed that magenta with the metallic swirl. 

He rifled through his paints, popping open different tubes and squirting a bit on his fingers, one color to a finger. Who needed brushes? Who the fuck cared? Back at his canvas, he slapped his hand down, splattering his face and hair with multicolored flecks of paint. He dragged his hand across the cloth, using his other hand to drag the other way. God, this felt so right, just letting the art make itself, rather than plan and agonize over composition and line. Real life didn’t need lines, so carefully drawn and stagnant. Real life needed explosions of color and chaos to keep it interesting and livable. Castiel remembered the corn fields on the outskirts of Pontiac, remembered how they drove him mad with their precise lines and monotonous sameness. Each line the same with its green stalks bleeding yellow up into the fine hairs that Castiel hated finding on his clothes after a long day helping the snot-nosed detasselers that were bussed out to the farm each morning in the scorching hot summer. He remembered the boring people of his small town, the even more boring people of his high school. He remembered how, aside from the one shining example that green-eyed girl had been in the seventh grade, all the people there were the same. The same clothes, the same taste in music, the same fucking everything. 

He couldn’t go back. 

Castiel hated how the choices he had made had defined him. He was a small town boy still trying to figure out the workings of the big city. He was a scrappy art student, struggling to make a name for himself in an overly crowded and suffocating scene, he was a whore for one of the richest men in Chicago, who paid to flirt outrageously with him, without even doing him the decency of taking his virginity. 

Dean. He needed Dean. 

The rush to his head was dizzying and cold in recognition that the man he wanted so desperately was not here. He glanced around the garage, at all the projects Dean was working on, covered by big sheets. The covered whatever-it-was over in the corner that Dean made him swear up and down that he wouldn't look at, even while Dean was gone for three days. The gray couch in the corner that Castiel was quickly getting _very_ familiar with, as it seemed to be one of Dean’s favorite places to fool around. The scattered tools that showed, while highly motivated and driven, Dean was a bit scatterbrained and tended to leave things where they landed, including, Castiel had to laugh, a pair of his own underwear from the last time they were down here together. 

Together, but not _really_ together. Dean wouldn't allow it. Wouldn't allow them to get closer than rubbing up against each other like horny sophomores in high school, desperate for any action they could get. Dean hadn’t taken it further than the last night Castiel had needed Dean to take control and stop what was happening. He'd said he couldn't trust Castiel if he couldn't even stay checked in enough to safeword if he needed. 

Castiel really was a screw-up. 

And it was so _fucking_ necessary that he be with Dean, that he stay with Dean. Castiel knew that there was no way he could leave Dean’s side voluntarily. That was why this entire tuition thing sucked so badly. Castiel needed Dean in ways he could never, ever articulate, and Dean didn’t seem to need him with the same savagery. Because it was just a job. This was supposed to be just a job, and Dean knew it too. He knew that Castiel wasn’t worth falling for, knew he didn’t have to risk contaminating himself with the dirty hooker, and why should he? Dean had money, a lot of it, impossibly good looks, and a loving family. Why would he ever lose himself and fall for someone like Castiel? It was just a job, and Castiel needed to start acting like it. This could all be gone tomorrow. 

Castiel turned to his canvas. This piece had a startling and completely unacceptable lack of green. Green would make it all better. Grassy, calming, mellow green. Green with a hint more of yellow ochre, pulling it more towards a Granny Smith shade. 

Green that was coming down the basement stairs, first looking expectantly happy, but then extremely concerned. 

“Dean.” Castiel breathed, before looking down at his hands and the mess around himself.

Shit. 

Dean approached him slowly, setting his briefcase by the stairs, his hands coming up like he was trying to get close to a spooked horse. Castiel looked around for a rag, anything to wipe his hands off. He hadn’t meant to make such a mess of… everything. 

“Cas, baby, what’s wrong? Were you—are you crying?” 

_Shit._

Castiel swiped at his face, knowing he was getting paint everywhere. Just what he needed, for Dean to think he had to take care of Castiel again, because Castiel was a stupid child way in over his head. Dean pulled his hands away, reaching back to grab a clean cloth from the workbench that Castiel hadn’t noticed before. Dabbing under his eyes, Dean cleared away the salt and the paint. 

The concern was still heavy in Dean’s eyes. “You gonna tell me what’s wrong?” 

“Fuck me.” Castiel knew he shouldn't ask, knew he didn’t deserve it. All of that didn’t stop him though. 

Concern was joined by confusion. “Cas…?” 

Castiel pushed forward, landing his mouth uncomfortably against Dean’s. He tasted like spearmint gum, which Castiel instantly hated the flavor of. He pressed in closer, trying to find the flavor of Dean underneath. Dean’s hands came up to his biceps, holding, but not quite pushing him away. His fingers swept slowly up and down the skin exposed by Castiel’s t-shirt, trying to soothe him. Castiel’s hands grabbed for Dean’s belt, pulling his dress shirt roughly out of where it was tucked. Dean grunted in surprise. Fumbling with the zipper, Castiel got his hand down Dean’s pants, where he found Dean disappointingly soft. Well, not for long. He started stroking gently, how he knew Dean liked. There was a haze forming in Castiel’s mind. He knew he wasn’t doing this right, but he couldn't bring himself to care. He had to have Dean, had to be had by Dean right now. Dean’s hands increased their pressure on his biceps, pushing him away now. He struggled briefly, but Dean was much stronger than he was. 

“Cas! Hold your horses, man. I just walked in the door,” Dean chuckled, though clearly still worried. “Mind telling me why you’re in my garage, covered in paint and tears, trying to rip my clothes off?” 

The hot push of tears that Castiel hadn’t noticed before was threatening again. “I—you said I could stay here—I didn’t—“ 

Dean blinked. “No, I didn’t mean it like that. Of _course_ you’re welcome here, baby. I mean—why are you so upset?” 

“M’not upset. I just missed you.” Castiel tried to push forward again to get to Dean’s mouth, but Dean folded him into a hug instead, wrapping his big arms around Castiel’s frame. Despite not getting quite what he wanted, Castiel melted all the same into Dean, hands clutching so tight in Dean’s dress shirt, he was surely wrinkling it. Dean shushed him, like one might to a small child. Stupid, Castiel thought to himself. 

“I missed you too, man. New York traffic is a fuckin’ nightmare. And that’s saying something, don’t you think?” Dean rocked them gently, kissing the top of Castiel’s head. Castiel knew he was being coddled. He knew that Dean was trying to distract him from getting down to business. 

“Dean, I really need you to fuck me.” 

The rocking stopped. “You said that. I think that’s something we gotta talk about, don’t you think?” 

“No. I don’t wanna talk.” 

Dean was hesitating, trying to talk himself out of it. Castiel used his position pressed to Dean to rub up against him, getting an erection rather quickly with Dean’s scent and warmth all around him. Dean must have felt it, because he groaned quietly, his own pants getting a bit tight. “Cas, I really think this is a bad idea—“ 

“Dean, _please_. You’re supposed to give me what I need, and I need this more than anything.” 

“Shit, fuck.” Dean’s strong hands suddenly clamped down on Castiel’s back, telling him wordlessly to jump. When he did, Dean grabbed his thighs tight, pulling Castiel into a rough kiss. Castiel carded his hands through Dean’s hair, pulling his head back to suck at Dean’s throat. Dean walked them over to the gray couch, depositing Castiel securely on the middle cushion. 

Castiel couldn't wait to get this man back on him, and made grabby hands at Dean, fully aware how ridiculous he must look. Dean, though, with his rumpled hair and feral expression, didn’t smile, didn’t react at all, aside from his heaving chest, staring down at Castiel. 

“Want you. Please, Dean.” Castiel whined, pitiful to his own ears. 

Dean hurriedly unbuttoned his shirt, tossing it behind him. He sank to his knees and roughly pulled Castiel’s legs apart. 

“Someone really did miss me.” Dean huffed a laugh, eyeing up the impressive bulge in Castiel’s sweats. He walked his fingers up Castiel’s thighs to the waistband of his pants, stroking softly over the skin. Castiel was positive that even his teeth were sweating with need and anticipation. Achingly slowly, Dean inched the sweats down Castiel’s legs, eyes roving over every inch of exposed skin as it was revealed, as if they had been separated for years, rather than just days. When Dean finally got the sweats down over Castiel’s cock, it popped up rather comically to it’s full standing position. “ _Ohhhhhh_ my poor baby. So neglected while I was gone?” Castiel couldn’t answer because he couldn't feel his tongue. “That’s okay, this isn’t going to take long. I can tell.” Dean grinned wolfishly and swallowed him down. Castiel keened, his mouth falling open. He squirmed, trying to get away, trying to get closer, he didn’t know. His eyebrows knit together, hands clenching into fists beside him. Dean’s hands came around to cup his ass, pulling more of Castiel into his mouth. 

“Dean—Dean, so good. Missed you so much—“ Castiel wasn’t even sure if he was making sense. This was it, he was going to get Dean’s cock in him soon. That would seal the deal, it would make everything better. Dean couldn’t leave him after that, right? 

Unless it made everything worse, and Dean decided he didn’t want to mess around with a pathetic virgin anymore. Dean’s tongue slipped down his shaft and then back up as Dean pulled off. He lapped at Castiel’s slit, causing Castiel to arch his back, hand coming up to grip at the back of the sofa. He was whimpering now. 

“Come for me, Castiel.” Dean whispered. And how could Castiel deny him anything? Although Castiel felt strung out and messy, Dean didn’t lose a drop out of his mouth. Castiel felt that his abdomen was never going to loosen up. When he finally calmed down, he felt Dean’s hand petting over his still-jumping stomach muscles. Dean still looked wrecked, but he smiled at Castiel. “Better?” Castiel nodded, and Dean stood up, rolling his shoulders and popping his jaw. He bent down to scoop his shirt off the ground, and walked over to the sink, turning it on to wash his hands.

Castiel had to try a few times to get his mouth to cooperate. “Are you still going to fuck me?” 

“Why are you so fixated on that?” Dean’s tone was carefully measured. 

“Because you said—“

“I don’t remember making a pinky promise to fuck you.” Dean snapped. Castiel fell silent. Drying his hands, Dean threw his shirt over his shoulder, going over to the stairs to grab his briefcase. “I’m going upstairs to take a proper shower. Come… get me if you need me.” He finished and started back up the stairs.

Oh no, the tears were coming back again. And this time, there was very little time for Castiel to stop them. Castiel stood up shakily. “So you don’t want to fuck me, is that it?” 

Dean stopped on the stairs, not turning. “What?” 

“Am I just too dirty for you to really fuck me?” He took a few hesitant steps towards the stairs. “Gonna go wash your mouth out to get the taste out off your tongue?” Castiel heard himself overreacting and didn’t try to stop it, he was too mad.

Dean turned, eyes flashing dangerously. “That’s what you think?” 

“I don’t know what else to think. You never do it. Sometimes you say you’re going to, but you never do it. Am I not satisfying to you?” 

“You’re seriously asking me that when I still have your come on my back teeth?” 

“Dean!” The tears were there, running down his cheeks. He didn’t mean to cry, didn’t mean to let this affect him so badly right here in front of the man he l—really liked. 

Dean sighed, coming back down the stairs. He set the briefcase down again and dropped the shirt on top of it. He came up to Castiel and wiped the tears away. Castiel wondered what he must be thinking of his sub right now, having to clean him up of tears twice in an hour. 

“Look, it’s not a big deal, okay?” Dean tilted Castiel’s head up to look directly at him. “We’ll get there. We just… haven’t… yet. It’s fine.” 

“But it’s what you want.” 

“I don’t want to do anything you don’t want me to do.” 

“Are you worried you’re going to hurt me?”

“Look, an we just drop this? Go upstairs and have some dinner or something?” 

“No, this actually really bothers me.” Castiel took a step back, watching Dean’s hand fall back to his side. Why was Dean acting so cagey about this? Couldn’t he see this was what he wanted? What he needed? “You won’t fuck me, you won’t take what you claim to want. It makes me wonder if you even want me at all.” Castiel spat the last sentence, positively furious now. Irrational as he was being, this was pissing him off, and right now, this was the last thing he wanted. 

Dean sighed and looked up at the ceiling. “Baby, of course I want you—“ 

“Then fuck me.” 

“I dunno if you’ve heard of refractory periods—“ 

Letting out a grunt of frustration, Castiel pushed against Dean’s chest, hard enough to knock him back a step. “Don’t try to make a joke out of this! Either you want to fuck me or you don’t.” Castiel took a breath, fire in his chest, and brought out the big guns. “You’re paying me for sex, aren’t you? That’s what you want? That’s why you dragged me into this mess.” 

Dean’s eyes instantly hardened, and he straightened up, putting himself at his full three inches above Castiel. “I am paying you for sex, aren’t I?” 

Castiel shrank back, equal parts delighted and terrified at the cold steel of Dean’s gaze. “Y-yes.” 

“In fact, I’m pretty sure that I’m paying to ‘boss you around’, aren't I? Isn’t that how you put it?” 

“Dean—“ Castiel stood there, mouth gaping like a fish.

When Dean suddenly stalked forward, Castiel had no choice but to step back, all but tripping over his own feet. “Seems to me like you’ve been getting a little mouthy lately, don’t you think? _Castiel_?” 

Sounding far braver than he felt, Castiel shot back, “What are you going to do about it?” 

Dean leaned way down into Castiel’s space, putting his face an inch from Castiel’s own. He could practically feel the way anger was rolling off of Dean in waves, let alone by the way his green eyes were flashing like a radioactive beacon. “Maybe I’ll put you on all fours and open you up nice and slow? Put my cock in you and go to town until you’re begging to come. Is that what you want?” 

God, that’s all he wanted. 

“Yes, Dean.” Castiel tried to put some force behind his words. He could feel himself getting hard again from Dean’s threats. He was going to do it this time. 

Dean tore himself away from Castiel. “Over the arm of the couch. Face down.” His voice was hard and unforgiving, booking no arguments. He hurried to comply. 

“Yes, sir.” 

“And take your pants all the way off.” Dean’s voice came from somewhere near the cabinets by the kitchen part of the basement. 

Now naked from the waist down, Castiel’s face was buried in the couch. He didn’t dare look up when he heard Dean’s footsteps return. He definitely didn’t dare even make a noise of complaint when the finger that Dean started rubbing around his taint and hole was cold with lube. Instead, he brought his arms up underneath himself, supporting his head on his crossed arms. He bit into his skin to keep quiet, feeling his cock harden up even more as Dean rubbed. There was hardly any friction from the lube, but the second Dean’s finger popped inside, Castiel make a muffled cry into his arm. 

“Don’t hide from me.” Dean said, just before the hard slap of a hand came down on his asscheek. Castiel’s surprised howl quickly turned into a moan. He wasn’t even faking it. He’d wanted Dean to get rough with him for so long, for him to want Castiel half as badly as Castiel wanted him. “You make such pretty noises.” Dean’s tone was less gravel now, and more sincere. Like he lost his edge for a moment. 

One finger quickly turned to two, Castiel pitching himself forward to try and get at least a little pressure on his cock. “Fuck me, fuck me please. Dean. Gotta come in me—“ Castiel was babbling. His face was so hot, pressed down into the couch like this. When Dean added another finger and pressed right against his prostate, Castiel was sure he was sobbing now. That was a completely new sensation and had him completely undone. He was grinding back against Dean’s hand, searching for that same feeling again. Dean must have been feeling merciful, because he jabbed into Castiel again and ground against that same spot again, holding Castiel on the brink of madness for a full ten seconds before pulling out again. 

Castiel tried to lift his head, “Wait—where are you… Dean—“ A hand came up to roughly shove his face back into the cushions. Customers had done that before, shoved his head down when he was sucking them off. He never liked it, but he took it because it was… a job. When Dean shoved his head down, his fingers stayed in Castiel’s hair, stroking roughly through it. 

“Thought I gave you an order, Castiel.” Dean growled. 

Dean was pissed. Castiel knew that. Dean was pissed off enough that he was only using Castiel’s full name, and he wasn’t letting Castiel look at him. That had never been in question before: if they were doing anything, they would do it face to face. While he thought it was weird at first, Castiel had very quickly learned to adore the closeness, and seek out more when he felt he wasn’t getting enough. That Dean was denying him that now said there would be hell to pay later. But how could Castiel complain about anything when he felt the blunt warm tip of _something_ pressing into him, achingly slowly. He grinned into his arms. He was finally getting what he wanted. Doing a quick full-body assessment, he came up grinning as well. He wasn’t panicking. He was really doing this! 

“Feels so good, Dean—Dean!” Castiel babbled on, pushing himself back into Dean. He heard a gasp in response and knew he had thrown Dean a bit off kilter with how much he was enjoying this. Inch by inch, Dean sank into him, filling him up in ways he had never experienced. By the time that Dean had bottomed out, Castiel was seeing stars, panting into his skin. 

Dean’s rhythm started slow, “Can’t get you all worked up for nothing, right?” he said. He pulled all the way out, and started his process of splitting Castiel open all over again. All through it, Castiel keened and whined, begging him to go faster. Dean kept himself carefully distanced that his thighs never hit Castiel’s ass, but at this point, Castiel was pleased to take what he could get. And what a getting it was. 

The faster that Dean went, the less control Castiel had over his mouth. He begged Dean to never stop fucking him, he praised what a good lover Dean was being and how good he was making Castiel feel, he made sure that Dean knew how much he was enjoying this. And it was the truth. Not a single part of Castiel was lying, and not for the first time since entering this house, he felt genuinely glad to be here, with Dean. 

Their pace couldn’t last, however. The roiling heat in his belly spread, causing the sensation that light was bursting through his fingers and toes, crashing him into his orgasm headfirst and whining loud and long when Dean pressed into him one last time, deep as he could go. 

Holy fuck. 

Castiel laid there, wincing only slightly when Dean pulled out, leaving him empty. Dean’s hands quickly stroked down his back, leaving a trail of fire after them. A shuffle of fabric told Castiel that his clothes had been picked up off the floor and deposited near his head on the couch. He couldn't make his knees work enough to lift himself up and grin manically at Dean. 

With more fabric shuffling behind him, Dean spoke, softly and with a tone that sounded almost like hurt. “Well, you got what you wanted.” Castiel’s smile fell of his face and he struggled to put himself on his elbows. “I’m going to take a shower.” Dean said gruffly, before the sound of his footsteps started fading. 

Castiel whipped around, exhaustion dragging him down the entire way, to watch Dean’s form retreating back up the stairs. He frowned. Things had seemed to be going so well? At least better than they had been? They’d both gotten what they wanted. Dean got to pound Castiel’s ass, and Castiel got Dean’s gorgeous cock inside of him. 

He glanced around, and saw an object sitting on the nearby coffee table that made his heart sink. A curved pink dildo, glistening with lube, lay on the surface of the table, so painfully clearly just in use. He glanced back at the stairs. 

He hadn’t gotten anything at all. 

And now Dean was upset. Why, he didn’t know for sure. He shouldn't have pushed Dean so hard for something he clearly wasn’t ready for. Where pleasure had previously sat so light in his stomach, dread and guilt came flooding into his system, weighing his insides down like tar. 

He pushed himself to his feet, shaky and uncoordinated. He had to make this right.

**Notes for the Chapter:**

> Just a reminder for all BDSM-ers out there, and ESPECIALLY the newbies. Do NOT scene while you're angry or upset. It's bad juju all around, and someone could get seriously hurt. 
> 
> Also! Do not underestimate the importance of aftercare! But more of that to follow! 
> 
> As always, thank you for reading!
> 
> -azo


	12. Interlude: Dean

**Summary for the Chapter:**

> Dean's story.

What most people don’t know about Dean Winchester is that he grew up around art. His mother was an artist. Now, to most four-year olds, anyone with the full 64 pack of Crayola crayons is an artist, but Dean knew his mother was pretty talented, even at such a young age. She specialized in paintings of angels. Big, huge canvases that could cover a wall, done almost entirely in watercolors. Dean’s favorite piece was an angel done entirely in shades of blue. Periwinkle tones for the wings, too floaty for their appearance; a cobalt gown dotted with lighter shades that made the fabric glisten; deep sapphire for the eyes, staring out at the viewer and following them from room to room. Dean remembers how long it took her to get the shading on the wings just right. He spent hours in her studio with her, pretending to be an art critic and telling his mom that her paintings were too pretty for the museum so they had to build her a new building, but that Daddy would build it for her. He remembered feeling scandalized when Mary would “accidentally” drip paint on him, causing her to laugh like a bell ringing while he swiped at his face, grinning up at her. The birth of the blue angel was a monumental experience for Dean to witness. He cheered when Mary announced that she was finally finished, and swooped down to scoop Dean up in her arms, spinning him around the studio. The blue angel seemed as much a part of their family as new baby Sammy, who was, in Dean’s opinion, a bit too small and stinky to really be considered a brother just yet. 

The blue angel was the last painting that Mary Winchester ever did. She died in a fire that swept through the Winchester mansion while John was away on a business trip a week later. Dean remembered all too well holding his baby brother in the back of an ambulance, while asking any fireman that would listen where his daddy was, and if mommy was going to be okay. 

Dean wasn’t sure if he had ever really recovered from that tragedy so early in his life, but the string of therapists he and his father had had finally asked him to stop coming after he kept trying to ask them about their own problems instead, calling him “remarkably well-adjusted for someone in his position”. Dean was better nowadays, really. He assured his dad of that whenever he asked, Bobby and Missouri too. He had family that loved him dearly, he was fine, really. He didn’t need someone in a dark office to try and unravel why he felt so much guilt without quite knowing why. 

What most people also don’t know about Dean Winchester is that he genuinely enjoyed his earlier days of his company more than his current ones. Sure, it sounds a little strange, who wouldn’t love the power, the prestige, the fine clothes, everything that comes with being one of the richest men in the bustling city of Chicago at the relatively tender age of 30? But the truth is that he misses the days when he and his secretary, Charlie, were operating their business out of a washed out storefront on the south side of the city. Most people wouldn’t even have believed that man, the one who had given up his parents’ fortune, made in the arms industry, to start this company with only his two hands (four including Charlie’s) and the $15,000 he’d saved from his own accounts since leaving college. 

It wasn’t that Dean was ever ungrateful for all his parents had given him, even posthumously. But between the legal battles with his grandfather, aunts, uncles, and cousins, and the overbearing pressure to go into the same destructive work as his father after his death when Dean was twenty, Dean was more than ready to slap a big sign over the Winchester family account that said “Use For Scholarships” and set up a trust account that he didn’t have to touch ever again. Instead, he took his degree, still from one of the best institutions in the country, and set out to make his own name. 

Winchester Holdings was a laughable name in those days. “Washed out store front” was the best descriptor for the tiny, drafty, piss hole he found. Back in those days, Charlie was less of an employee, and more of a friend who kept track of his schedule and also knew how to fix a computer. He was so damn proud of that place, though. Because it was his. His first contracts were businesses even smaller than his, ran out some guy’s garage, just trying to do some good in the world and help a few people out of nasty situations. That’s what he tried to do too. Help the little guy stand up to the big guy. Now that he was the big guy, he tried to stick to that original mission as best he could. He hated to see people taken advantage of, either by individuals, businesses, or even the law on several occasions. His company was a reflection of the lease on life he found after his parents died: Find some good in the world, and help it grow. He liked his little business, and his little paycheck, even if it was a downgrade from his youth. 

But then his business stopped being so little. Dean still wasn’t sure how he happened on the deal with Amnesty International, not sure how he had attracted the attention of the massive organization, too big to even be contained by one country. But one deal with them, and he was set for life… again. It was almost too easy. The little guy was now the big guy, but the big guy still had the little guy’s back, and now he had the funds to back it up. Dean could suddenly hbuy Charlie the technology department she always wanted and hire her the secretary she always deserved. Now their board meetings took place in an actual conference room, with actual matching chairs. 

But even with all the upgrades, he was a lot more impersonal in his dealings now. He didn’t get the pleasure of meeting his clients in mom n’ pop diners, or the coffeeshop down the street with a killer black brew. He had an entire wing of the building to keep track of his clients, instead of his secondhand rolodex he picked up from the consignment shop. The money was there, but the love was gone. And while he was proud of how many people he could help, he sometimes wondered about the depth of help his people actually got. He had made a name for himself, but over time, that name had changed back into the high-class glamor the Winchester name used to carry. His only consolation was that his name now meant an innocent client walking free, rather than a shipment of weapons was incoming. 

What people finally might not know about Dean Winchester is that he is lonely. He missed going out with Charlie on Fridays to the hole-in-the-wall dive after work. They no longer reveled in their weekly ritual after Charlie moved in with Gilda From Accounting™ and Dean had more meetings to go to than time for bar crawls. He had his big house, far too big for just him, since he had fired most of his staff for being incompetent—“They can’t be incompetent if you don’t tell them how you want stuff done!” “She touched my car, Sammy!”—and one shouldn't go looking for love in a boardroom. But he was young. He was 30 years old, had all of his parents’ devilishly good looks, and a sexy-ass car to boot. The problem had to be with him, right? 

In all honesty, he hadn’t been looking for someone like Castiel. Even with all the money he had ever wanted, he never thought to spend it on cheap love. Sex was fun, sure, but buying it off someone just felt dirty. Like he wasn’t deserving of their affections. And yeah, Dean tended to get clingy after sex—he was a tactile person, sue him!—which made the prospect of getting an escort all the weirder. Dean had this old notion that sex meant love. He knew it was old fashioned, and he regularly got teased for it by his college buddies and more, but it was how he and his brother had been raised. If you didn’t love someone, you didn’t do the deed with them. Dean was sure that his mother had only been trying to prevent any shotgun weddings—hey, her kids were lookers, and she knew that early on—but the lesson had stuck with him. Of course, he’d bent the rules a bit from time to time; ‘love’ was a fuzzy concept at best. You could fall in temporary love with a stranger, and who would deny a pretty stranger a night in the back of his car? He’d made countless people fall to pieces with pleasure, because of the magic of a few shots of tequila, or the right song in the right bar. He loved making people feel good. He’d only really fallen in love a handful of times, though. He was determined not to fuck it up anymore in his “grown up years.” He just didn’t have the time anymore. He loved getting to know people, even more now that he hardly had time to have a proper conversation with his secretaries, loved talking with them about anything. He craved human contact, would do anything for some human touch. 

And that wasn’t even broaching the subject of his love life. ‘Relationships take time.’ He’d told Sammy this every time he’d asked when Dean was going to settle down. He’d told Missouri this when she’d asked if he was really planning on spending Thanksgiving alone again. He’d told the media this when a photograph of him and a certain perky blonde heiress splashed across every tabloid in the area, speculating on his status. He didn’t have the time required to make a solid relationship work. There was always something in the way, meetings, business trips, court hearings, her job (or his job, Dean was about as equal opportunity as it got when it came to sex), something that made the relationship fall apart right around the two-week mark. Yeah, Dean wasn’t trying to circumnavigate the obvious. He simply didn’t have time. 

It was his first day off in over three months. Not the first time that his secretaries had all but shoved him out the door with explicit directions to “take a fucking break,” but the first time they’d ended the demand with, “Mr. Winchester, sir.” He attributed that to the mean expression he’d been wearing unconsciously for most of the week prior to this. He also had a rock-solid promise from his secretaries to hold down the fort while he was gone for a full twenty-four hours, and a pinky promise from Jeff, one of his newer secretaries, to keep Becky from redecorating his office while he was gone. At first he hadn’t known what to do with himself. He tried golfing with his buddy Mark, from Goldmann, but Dean was pretty lousy at golf, so they’d called it quits around noon. He tried working on his cars, but the garage felt too dark and quiet for such a nice day. He took a walk around the city, finally went to Millennium Park for the first time since he’d moved to Chicago nine years ago, bought himself a snow cone, and played photographer for little families of tourists, reveling in the prospect of doing nothing. He caught a city bus for the first time in five years and chuckled at how the fabric of the bus seats hadn’t seemed to change. When he got back to his house, he asked Missouri to actually have a sit down dinner with him. They’d talked about the flowers in the greenhouse (Dean forgot he had a greenhouse) and the faucet Missouri couldn't seem to fix. She’d also promised to make breakfast tomorrow morning before his meeting at eleven. He’d thanked her profusely and given her the rest of the night off, swearing up and down he’d be at the breakfast table the next morning. 

With his free evening, slunk around his house for a bit longer, then remembered he didn’t have to go to work at the crack of dawn the next day. He’d taken three minutes to pull on his second rattiest pair of jeans (his oldest pair were strictly for working in the garage) and his favorite leather jacket, and hightailed it down his driveway and to the south side of the city to his favorite dive bar from back in his glory days. He ordered a whiskey neat, and threw the pretty bartender a wink while he settled in to people watch. 

He hadn’t meant to run into someone like Cas, he didn’t mean to single the young man out of the crowd. But the mess of dark brown hair, coupled with the enormous bright blue eyes made him fairly hard to miss. He was thin, Dean noticed, and he was pretty sure it wasn’t because he watched what he ate. Dean had a feeling this guy had had some tough luck. He kept looking around like he was waiting for someone too. Dean found that to be a shame, but unsurprised that someone who looked like that (that jawline though) could be alone for long. 

When the young man got up to leave, Dean could hardly believe his luck when the man’s next move was to approach him next. Was Dean really that much of an easy target? 

“Break my heart and tell me your date’s waiting for you out in the car.” He said, smile playing across his face as easily as the slight blush he could feel crowding up underneath his jaw. Play it cool, Winchester. 

“No, change of plans,” the man had said. “I’ve got a free evening.” Oh shit, the guy was playing along. He asked if Dean’s date was coming, like he was intruding on something. Dean said he was free too, and then the man had dropped the bombshell. 

“Do you want me to suck your dick?” 

Dean was pretty sure he was going to choke to death on his whiskey right then and there from sheer shock. This conversation took a wildly different turn in the two seconds they had been talking. It was then that he figured out what the man, Castiel he’d later learned, was after. 

Castiel was a fucking virgin. Dean would have thought he was lying, but there was something about the kid that looked entirely too innocent to be playing whatever dangerous game he had going out on the streets. Dean believed him wholeheartedly. Even more so, after he witnessed the near-panic attack Castiel had while gearing up to sleep with him that first night. Dean wasn’t sure what he was thinking, inviting Castiel to spend the night at his place after making him an offer to essentially be his sugar daddy, but he knew he was more than gleeful when Castiel agreed to think about it. 

Lying in his bed that night, Dean stared up at the ceiling, considering his night. This was the good in the world, right here. Castiel, the painter, was the blue angel Dean hadn’t ever known he’d been looking for. Dean had to help him, had to help Castiel grow his own good in the world. He didn’t want Castiel just for the sex, or anything like that. There was something about Castiel that kept catching him off guard whenever that gaze turned on him. Dean could already tell Castiel was going to be a world of trouble for Dean, he just didn’t know how yet. But Dean had never been one to run from trouble, and it seemed that Castiel wasn’t above causing a bit of hell on his own. 

Practically a match made in heaven.   
And now Dean was pretty sure he was fucked ten different ways. Castiel had turned out to be everything Dean hadn’t known he was missing. The kid had a wicked sense of humor, painted like the gods dared him to, and was so damn responsive to Dean’s affections. They had fun together, both sexually and not. Dean loved watching Castiel paint, loved listening to him explain color theory or rant about oil paints (Dean had never met anyone with such strong opinions on such seemingly insignificant details), loved just watching Castiel be. He knew he was just a client to Castiel, how could he be anything more? That didn’t stop him from coveting the time he had with Castiel, didn’t stop him from wanting to spoil him absolutely rotten just for being Castiel, even if Cas had a habit of arguing when he thought the gift was too generous. 

In short, Dean was pretty sure he was in love, and very sure he was in trouble. 

He still hadn’t fucked Castiel, hadn’t crossed that line. Even though he was more than willing, and reasonably sure that Castiel wanted it at least most of the time. But there were still moments when Castiel would lock up and panic, which told Dean that Castiel was definitely not ready, no matter how much Castiel tried to convince him otherwise. Dean had had more than enough clients with that kind of agency taken from them by force, without someone there to make the decision to hold back until they were well and truly ready, he wouldn't dare take that from Castiel. It was enough for Dean to suck Castiel off until the kid was writhing and swearing, enough to make him shiver when Dean pressed kisses along his collarbone, enough to watch the lust balloon his pupils wide and dark when Dean sank to his knees or pulled him in by the belt loops. He loved making Castiel feel good, and took his own pleasure from how well Castiel was being taken care of. 

It wasn’t a hardship whatsoever to whip out his checkbook whenever Castiel needed him. Because he knew that’s all the good he served Castiel. If they were in a different life, if Castiel was a successful artist all on his own, he wouldn’t have looked twice at Dean. Dean knew what his place was in Castiel’s life. Castiel belonged in an art studio, surrounded by his work, with acclaim and fortune waiting at his door, not on his knees at Dean’s feet, hidden away in his garage. 

And how could Castiel ever doubt that? How could he doubt how fucking crazy Dean was for him? When Castiel accused him of wanting to wash the taste the taste of Castiel out of his mouth, Dean had been absolutely boggled. Did he really think that low of himself? Of what they had? Something inside Dean had snapped at that. He wasn’t proud of it, not by any means. He knew he should have stopped, should have come to comfort Castiel instead of rile him up like that, only to deceive him. But he was angry and frustrated, at both himself and at Castiel for daring to think his time meant anything less than the world to Dean. 

Dean knew he’d have to throw that dildo away. Castiel was sure to leave him when he found out what he’d done, and he'd appreciate as few reminders of what could have been as he could manage. He couldn’t save the blue angel, and for that, he had to work with what he had. 

Something else that people might not know about Dean Winchester, is that it doesn’t matter what kind of punishment people might inflict on him, because he will always be able to hate himself more.

**Notes for the Chapter:**

> Thank you for sticking with this story, even though the weird posting schedule, and the emotional highs and lows. I appreciate every time you comment and leave kudos on this story. It has truly been a pleasure to write for you. 
> 
> Thank you.  
> -azo


	13. But If You Try Sometimes, You Get What You Need

**Summary for the Chapter:**

> Forgiveness, can you imagine?

**Notes for the Chapter:**

> Happy Halloween for those of you who celebrate that sort of thing! 
> 
> I must ask of you, humble reader, one more time to forgive me in my lateness in posting this chapter. As usual, I am faced with the reality that writing is hard and takes a lot of dedication that I am not always prepared to give. I trust that you have not lost interest, either in me or in this story, and that you will be as delighted to read this, as I was to write it. 
> 
> Thank you.  
> -azo

Castiel hurried up the stairs as fast as he could on still-shaky legs. He had to give Dean credit; even if he hadn’t gotten fucked like he wanted to, Dean could still dish out a hell of an orgasm. Castiel felt another pang of regret at the thought of Dean not getting any pleasure out of their encounter at all. Dean had just come downstairs because he had heard Castiel in the garage, he had wanted to say hello after being gone, and Castiel had ruined it. Ruined it, like he had a shining tendency to do. He almost ruined his chances of getting into the Institute all those years ago, he almost ruined any chance he had with Dean within the first 48 hours of even knowing the man, and now he was about to ruin this one good thing in his life besides painting because he was feeling a bit impatient. 

Turning the corner at the top of the stairs, he caught his foot on the leg of a table and was sent sprawling to the ground. Castiel glanced up and noticed a pair of very sensible work boots standing a foot from his face. He scrambled to his hands and knees and looked up at Bobby, who was blinking down at him with his usual and perpetual scowl on his face, and his omnipresent ball cap on his head. 

“Better slow down, son.” Bobby said, reaching down to help Castiel to his feet. 

Castiel leaned back on his heels when he was upright again. “Have you seen Dean?” The words came out in a rush, bordering on unintelligible with their urgency. 

Bobby’s frown deepened, his weary eyes tracking up and down Castiel’s form. Suddenly, Castiel was made horribly aware that his rumpled clothing and fucked up hair, coupled with the telltale blush in his cheeks made it very apparent what he had been doing not fifteen minutes before. “He stalked past me ‘bout five minutes ago, lookin’ like the world had just come down on him. You boys okay?” 

Still unsure how much Bobby knew, or how much he was allowed to tell Bobby, Castiel tried to paste a reassuring look on his own face. “He’s just tired, I think. I just want to—to check on him.” 

Bobby raised an eyebrow, clearly not buying any of that for a minute. “You have a fight or something?” 

“I—we—“ 

“Can’t remember the last time he looked that upset, ‘cept maybe when he and Lisa broke up.” Bobby looked down at him, suspicion high in his eyes. 

“We’re not—it’s not… like that.” Castiel stuttered. He knew how Dean liked to keep their life together fairly private. And really, Dean was a client. There should be nothing more than professional concern. Colleagues, maybe. Not quite peers, but also not quite regular friends. 

The way Bobby’s face darkened told Castiel that 1) that was the wrong answer, and 2) Bobby knew better. Castiel sighed, slumping where he stood. 

“I need to talk to him and figure out how to make things better.” 

“I don’t mean to pry, but Dean’s a good kid. Kinda headstrong sometimes, and stupidly loyal… but he’s good.” Bobby said sagely. Castiel raised an eyebrow, wondering why Bobby chose now to tell him this. It wasn’t like he was unaware of what a good man Dean was. It was one of his favorite attributes about Dean. Bobby continued, “He’s also been through a hell of a lot, so you’d best not be making it any worse.” A glint sparkled in Bobby’s eye, and Castiel understood. He was just given a shovel speech by his sugar daddy’s gardener and pseudo-uncle in the hallway of a multi-million dollar home in his ratty sweatpants. 

What a life. 

“Trust me, I know what a good man he is. I wouldn't be standing here if he wasn’t. But I just—I really fu—messed up, and I need to make it right.” Castiel felt a bit of the overwhelming desperation he felt leak into his tone. Bobby’s face softened, apparently convinced. 

After a moment of silent assessing, Bobby spoke. “He’s up in the kitchen I think. He can’t cook for shit, but it never stops him from trying.” 

Castiel grinned weakly and skirted around Bobby, heading up the hallway, past the foyer. He noticed Dean’s favorite blazer draped over the chair, where he hadn’t even bothered to hang it in the hall closet like usual, he had been so eager to get downstairs. Castiel’s heart clenched again. Just before he entered the kitchen, he heard the sound of AC/DC coming softly down the hallway. Dean was a funny person, in that someone could usually tell how he was feeling by the volume of the music he played. When he was happy or excited, the music was at ear-shattering levels. Castiel hated being in the same room when he was like this, but couldn't stand to be far from Dean’s infectious smile and attitude. When Dean was upset, he played his music at more reasonable tones, suitable for a normal person listening casually in their car. When Castiel found Dean in the kitchen, the music was around a tenth of its usual volume. 

Dean stood at the island facing away from the door, mixing a bowl of what looked like chocolate batter. The red box to the left of Dean’s setup told Castiel that he was making brownies with zebra frosting, Dean’s favorite dessert besides pie. 

Castiel knocked on the door frame, not wanting to startle Dean. He watched Dean’s shoulders instantly pick up ten kinds of tension that Castiel immediately hated. 

“Come to yell at me?” Dean asked, not bothering to turn around. He did reach out and turn the music down, however. 

Castiel sighed and came to stand on the other side of the island, giving Dean all the space he could. “I wasn’t planning on it, no.” He leaned his elbows against the counter. “Do you want to be yelled at?” 

Dean finally stopped stirring and looked around. “What?” 

“You always give me what I want, even if it’s not necessarily what you want. I can return the favor.” 

Blinking, Dean put his mixing spoon down and turned towards the island. “Cas—“ Castiel silenced him by reaching across and cupping his face, putting his thumb against Dean’s mouth. Dean grabbed his hand and held on, not moving Castiel’s hand, but staying connected all the same. 

“Just—I’m sorry,” He pressed a bit harder when Dean opened his mouth to try and speak. “I’m sorry that I tried to pressure you into something you’re clearly not comfortable with. I don’t pretend to know why, but I promise it won’t happen again… if you still want me—“ 

“—I want you.” Dean said suddenly, his eyes getting bigger and more panicked the longer Castiel talked. Castiel smiled sadly and hushed him. 

“I’m glad. I just wanted to thank you for taking such good care of me all the time, and I missed you.” 

Dean slid Castiel’s hand away from his mouth, but not before pressing a quick kiss to the pad of his thumb. “Missed you too, you know.” 

“Do you—want to talk about it?” Castiel ventured without really knowing if he wanted to have this conversation. Dean could say that he wanted Castiel until he was blue in the face, but Castiel knew that he didn’t deserve a scrap of Dean’s time or affection. Not with the way he’d acted. 

Dean hesitated, but shook his head. Castiel looked away and nodded, pulling his hand back, where it felt cold without Dean’s breath. 

“I’m going to go take a shower, and then maybe head for bed. In my room.” He backed away from the island and started towards the door. 

“I don’t deserve you, you know that?” Came Dean’s voice from behind.

Castiel stopped, his hand on the doorknob, unsure of what he just heard. How on earth could Dean ever think that he was something Dean didn’t deserve? He knew he played that card all the time, trying to make his time seem worth the price to Dean, but he knew. He wasn’t anything special. And Dean was so special. So special that the words Dean was saying didn’t even make sense. 

He turned around. “Dean—“ 

Dean plowed on, looking fairly lost with his hands dangling loose at his side. “I don’t. That’s just a fact, man. You are… miles too good for me.” The corner of his mouth twitched, not in a smile, but into what Castiel thought was a wince, quickly reeled in. “And someday, you’re gonna figure out that you deserve someone who can give you what you want, and you’re gonna leave.” 

Castiel struggled to swallow around the sudden lump in his throat. “Do you—should I leave, then?” He looked down, and struggled to get himself together. If Dean sent him away right now, he wasn’t sure if he could ever forgive himself for hurting this wonderful, but delusional man in front of him. 

Instead, Dean reached a hand out to him, before quickly drawing it back. “No, that’s the sick part.” He laughed humorlessly. “I never want you to leave… ever.”

“I won’t. I’m right here if you want me to be.” 

Dean staggered forward, backing him up into the wall next to the door. Castiel felt his breath catch in his throat. “I’m serious, Cas,” Dean continued, reaching up to bracket Castiel’s face with his hands on the wall. “I would pay for school… for anything, forever if it made you want to stay here with me.” The look in his eye made Castiel wary. There was a brightness there, yes. But it was all wrong. Manic. Frightened. 

Castiel slid his hands up Dean’s chest to his biceps, clutching them with the depth of the emotion he was feeling. “Maybe you should go lie down and get some rest. You’re not making a lot of sense, honey.” Castiel winced as he heard the pet name come out, but Dean either didn’t notice or didn’t care. 

“Will you come with me?” Dean’s eyes were wild, boring into Castiel’s. 

“You want me to?” 

Dean didn’t answer, but nodded tightly. 

“I—yes.” 

“O—only if you want to,” Dean choked out. “I don’t want to make you feel like you—like you owe me anything.” 

Castiel thought, like he had thought many times before, that it was laughable to think that he would deny this man anything. He gripped into Dean’s shirt harder and felt his resolve solidify. 

“Come to bed with me, Dean.” 

Dean leaned forward and pressed his forehead against Castiel’s. 

…

 

For all the electric tension from earlier, they fell into walking and kissing like they had been breathing the same air for decades. Castiel tugged Dean towards the master bedroom, taking every opportunity to press the other man against the wall along the way. Dean gripped his hips possessively, his tongue staking a claim with every kiss. When they finally reached the bedroom, they took turns divesting each other of articles of clothing, breaking apart only for the seconds it took to get their shirts off. 

“Wanted this the whole time I was gone,” Dean whispered against his mouth. “Missed you so much.” 

Castiel shivered in delight at his words, relieved beyond measure that Dean wasn’t firing him or kicking him out, thrilled that he could still have this. 

Dean’s huge hands cradled his jaw, thumbs tucked in the dip in front of his ear. When Dean’s tongue slipped inside his mouth, Castiel obediently opened his jaw wider. Dean pressed in harder, keeping it open with his own mouth. 

“What do you want?” Dean asked, pulling away after a moment. Castiel shuddered with the knowledge that Dean would arguably give him whatever he wanted right now. Even if Castiel asked him to fuck him, really and properly fuck him, Dean would probably say yes. 

Which was why Castiel said, with conviction, “I just want you to keep kissing me.” 

“Take a shower with me?” Dean pulled away slightly, leaving a string of saliva between them. “It was a long flight and—“ 

Castiel pushed forward again, cutting him off. Dean seemed as completely enamored with the way their lips came together as he did, not wanting it to end any time soon. “‘Course I will.” Castiel whispered. 

Dean tugged them towards the ensuite bathroom. They both stumbled briefly over the pile of clothes left on the ground, but neither stopped to pick them up or to even stop kissing to look where they were going. When their feet hit cold tile, Dean promptly backed Castiel up to the wall nearest the all-glass shower. The tiles felt almost unbearably cold against Castiel’s skin, but the heat Dean was throwing off in front of him more than made up for it. Dean reached behind himself to start the water. In no time, the whole room was filled with steam, though Castiel thought it should have taken far longer with the size of the space. Wealthy people, honestly… 

The air felt hot and muggy, causing sweat to slide down their bodies, even before they stepped into the water. Dean had his hands all over Castiel’s body, and Castiel wasn’t trying to hide from him. Wasn't trying to put distance between them, wasn’t trying to put on a show. There was nothing to be ashamed of in this space, in this hidden corner of the world where it didn’t matter that Castiel was being paid for his time, or that Dean was clearly dealing with a whole host of issues of his own. When Dean lathered Castiel’s hair with soap and raked his fingers through, it felt like a benediction. A respite. Castiel tipped his head back to lay on Dean’s shoulder, and Dean gave up any pretense of keeping this shower relatively clean. He nipped at Castiel’s throat and ran soapy hands up and down Castiel’s chest. He palmed Castiel’s erection and made it slick, practically frictionless in the light grip Dean kept on him. In no time, Castiel was grinding forward, eager for more, murmuring his approval into the space between the damp air and the hot skin of Dean’s throat. Dean kept up a litany of his own, his Adam's apple bobbing against Castiel’s lips. 

“Missed you every single day. Missed this—want you every day, just like this—you 'n me, Cas.” Dean’s hand squeezed him lightly, ramping up the pressure on his cock into something positively incendiary. Castiel felt his mouth open in a gasp, but heard no sound come out. He reached his arms up and stroked over Dean’s biceps, relishing how the water made his skin slippery and warmer than usual. He could feel Dean’s cock pressing insistently into his ass, not asking for entrance, but always making its presence known. 

Dean’s hand sped up again, leaning into Castiel as hard as Castiel was leaning back into him. Castiel was sure that they would topple over at any moment. His fingers scrabbled around Dean’s hairline, digging in at the sensations that were ripping up and down his spine. It always felt good with Dean. Always, always, always—

Castiel came with a shudder that tore a high sound from his mouth. He felt Dean thrust against his backside a few times before his ass was covered in Dean’s come as well, an almost pained grunt sounding from behind. 

Slowly, Castiel turned around, his arms coming up again to wrap around Dean, not caring if he was being clingy or anything that would prevent him from having this moment. They kissed languidly, their tongues sliding against each other in the slick of saliva and water alike. 

“Just got you clean,” Dean said, his lips moving against Castiel’s. “’N then you go and get yourself dirty again.” He smiled. 

Castiel nipped at his lip. “That’s not entirely my fault, is it, Mr. Winchester?” 

“Don’t call me that,” Dean said sharply, but immediately pressed an easy kiss to Castiel’s lips to soften his words. “Not now. I don’t—I don’t want to be that guy right now.” 

“Whatever you want.” 

Dean pulled back a bit with a faraway look in his eye. He reached behind Castiel and turned the water off, the bathroom around them fading into silence. “I just mean—that you don’t have to call me that, you know?” 

Castiel nodded, nonplussed. “Got it. Stick to ‘Dean' or ‘Sir’.”

Grimacing, Dean looked down at the shower floor, still swirling with soap as it all ran down the drain, along with the evidence of their not-so-clean shower. “Yeah, sure.” He pushed the shower door open and stepped out, not letting go of Castiel’s hand until they both had towels to dry off. Castiel was still confused. What else was he supposed to call Dean if he was suddenly getting choosy about what he preferred? 

Reaching out, he placed a hand on Dean’s arm. Dean looked back with a smirk on his face that Castiel saw through in an instant. “You don’t like those either?” 

“I just—“

“What do you want me to call you?” 

Dean sighed and looked at the ground. “I dunno. It’s fine, it's not a big deal.”

“It is a big deal if you feel bad about it.” Castiel tightened his grip. He’d already almost lost this man to miscommunication, he wasn’t about to recreate the same feat twice in a night. 

“I just think it sounds a bit… impersonal is all. Kinda like I just—I dunno—picked you up right off the street.” Dean shuffled his foot, kicking up a bit of water that had puddled under their feet as they dripped. 

Castiel tilted his head and squinted. “You did, Dean. If we’re being technical.” 

“Right,” Dean said quickly. “So it’s not a big deal.” He turned, towel slung around his hips and stepped out of the bathroom into the bedroom. He crossed to the dresser and pulled open a drawer, fishing out sweatpants and t-shirts for the both of them. He handed both of these, along with some clean boxers, to Castiel, keeping his back turned through this interaction. He stepped into the boxers, and quickly pulled the sweats and t-shirt on, shielding himself from view and from the tension Castiel felt creeping around. 

Knowing he’d said the wrong thing _again_ , Castiel crossed the room, still only in his towel. He stood deliberately in front of Dean, taking both of his hands and squeezing them in his own. 

“You want this to be more personal. Like a relationship,” Castiel searched Dean’s face for an indication of… something—disgust, relief, _anything_. “You want to treat me like a boyfriend.” 

Dean’s jaw set so hard, Castiel could practically hear the teeth grinding. “Look, Cas—I’m really sorry if this makes you uncomfortable. I get it if you just want to keep it professional…”

“I didn’t say that I minded,” Castiel tried to catch Dean’s eye, tried to get the man to look at him. “Just an observation. Making sure I understand what you want.” 

Dean didn’t say anything for a while. His gaze switched between Castiel’s eyes and mouth for a bit, searching for something. Whatever he found there, made him smile shyly and look down at their feet. “You feel like a boyfriend sometimes. We fight like boyfriends.” 

“I thought relationships took too much time.” Castiel’s voice felt raw. 

“They do. That’s why I don’t usually find myself in this position—wanting this… ever.” Dean’s face was so earnest, Castiel couldn't help but believe him. Dean was drowning in this just as much as Castiel was. That knowledge lit Castiel up from the inside. 

“So, just so we’re being totally clear—we still want to keep the arrangement, right?”

Dean nodded emphatically, squeezing tightly on Castiel’s hands. 

“We’re just…changing some of the dynamic?” 

Again, Dean nodded, meekly this time. Questions hung heavy in his eyes, like he was afraid to look too eager for this, lest Castiel leave him here. 

“Then it’s set.” 

“Yeah?” The corner of Dean’s mouth ticked up at the side as the light that Castiel loved so much flooded back into the green of his eyes, making them glow. 

“Yeah, and for the record,” Castiel leaned in close, going up on his toes to get right by Dean’s ear. “You feel like a boyfriend, too.” 

Castiel didn’t get a chance to see the smile on Dean’s face, before it was pressed into his own and he was pulled down onto Dean’s massive bed.


	14. Caught in a Bad Romance

**Summary for the Chapter:**

> Slice of life, with a heaping helping of reality.

The silence that followed wasn’t the kind that Castiel was used to. He remembered being in grade school and dreading the natural silences that would come up in conversation, especially on the phone. One second, you’re asking Aunt Judy how the weather’s been in Alto Pass, and the next you’re grappling for something to say, cringing internally at how tortuous talking on the phone can be. He remembered the first and only time he helped out in one of the freshman level art classes at the Institute, because his favorite professor had asked him to. They had all stared at him silently, jewel-toned hair flopping into their eyes as they contemplated his question. He worried they might see him sweat through his Very Professional Button Down. He remembered that terrible moment after he finished off his first client in the bathroom of a Gas N’ Sip on the west side of town. He didn’t know what to say, and neither did his john. They looked at each other for an uncomfortable thirty seconds, before Castiel gave an awkward “See you around,” and hightailed it out of the stall. Those were all bad silences. Cloying, and pressing. 

The silence with Dean was so much better than all of those. 

As he lay on the bed with Dean, television switched on lowly in the background, Castiel could feel himself drifting off. Dean’s hand stroked up and down his arm slowly, seemingly unconscious on Dean’s part. Whatever was said about Dean—his car hobby, his business dealings, whatever—let it be known that Dean Winchester initiated 99% of the physical contact between the two of them. Castiel wasn’t even sure what program was playing on TV, or even what time it was. He rolled so that his face was pressed into the contour of Dean’s shoulder and closed his eyes, huffing a contented sigh against Dean's warm skin. Dean’s arm tightened around his shoulders as the man pressed his cheek against the top of his head. 

“Hey…Cas?” 

Castiel made a sleepy sound to show that he was listening. 

“You know that—it’s not that I don’t want to fuck you… you know that, right?” 

Castiel sat up, the silence shattered. “We don’t have to talk about that if it makes you uncomfortable.” 

Shifting to sit up more fully, Dean pulled his arm back and turned to face Castiel. “No, you deserve to know. And I always make you talk through shit too, so we’re even, okay?”

Castiel leaned down and fished around for his clothes. This felt like a Shirts-On™ kind of conversation. 

When Dean opened his mouth a few times, without words coming out, Castiel reached out and took his hand. He smiled reassuringly when Dean looked up. Dean took a breath. “When you told me you were a virgin… that no one had ever had their hands on you, I was kinda…” He looked like he was searching for the right word. “…taken aback, I guess. You’re a good looking guy and I thought maybe you were just lying to reel me in. But…” Dean shook his head and huffed. “The way you responded to me that first time—in my living room, you remember?” 

Castiel hung his head. Yes, he absolutely remembered the way his body betrayed him, giving away how nervous he was, to the point that Dean thought he was having a panic attack. Which, in all fairness, he almost was. “Can we just leave that out of the story?” 

Dean smirked. “I figured no one could fake being a virgin that easy. And the bad thing is that I liked that no one ever touched you before, because it meant… it meant I could be the first.” Dean suddenly looked up, stricken. “I know that’s stupid and old-fashioned, and it shouldn’t matter, but it does—it… it did.” His eyes pleaded with Castiel to understand. To not run away. “I was ready to be the one to introduce you to all this study and the challenge of it was more attractive than I can say.” 

About to interrupt, Castiel opened his mouth. Dean continued, a flush rising on his cheeks. 

“I dunno… I look at you, and I see what a cool kid you are… and I don’t want your first time to be with some guy who’s paying you for the chance to get in your pants. Like, yeah, I’m more than willing to help you—whatever, expand your horizons or whatever. And I know this sounds really archaic of me, but… your first time—your first real time—it should be with someone you love. Someone who’ll take care of you. I dunno.” Dean looked down at where he had drawn his hands into his lap. He rubbed his own thumb over his palm in a nervous gesture. 

Castiel put his hand on top of Dean’s clasped ones. “You do take care of me, Dean. In all the ways that matter. I feel safe here. I trust you.” 

The smile that crossed Dean’s face was neither happy nor relieved. “I’m still paying you, Cas. It’s different. It imbalances us. You should save your first time for someone you love. In my opinion.” 

Tilting his head, Castiel spoke after a moment. “You do realize I’m a sex worker, right?” 

If it were possible, Dean blushed even harder. “Yeah, I get it—so you see why I feel so stupid trying to… to save you from this, right?” 

“Was your first time with someone you loved?” Castiel asked. 

“I thought so.” 

“Was it a man or a woman?” Sue him, Castiel was curious about Dean’s history. 

Dean smiled for real this time. “Her name’s Amanda. We met in my first year of college. We’re still acquaintances, but not much more than that. Think she’s married with two kids in Sacramento.” 

“Thank you for telling me, Dean. For helping me to understand.” 

Castiel was unprepared for the tenderness in Dean’s eyes. “Sure thing.” 

“So, what do you consider a ‘first time’? Just so I know what to avoid.” 

Dean rolled his eyes. “You know exactly what I mean, smartass. Don’t make me spell it out for you.” 

“Sure. Outright penetration is a no-go, right?” 

“I will buy you a new car to never use that word in this context ever again. Jesus, yes, it’s a huge no.” 

Castiel ignored the threat of a new car.“Even if you want to treat me like a boyfriend?” 

“… yes. Still a no.” 

He swung himself across the bed into Dean’s lap. He hovered his face a few inches beyond Dean’s and pitched his voice low and intimate. “Does kissing count?” 

Castiel had the wonderful pleasure of getting to see Dean’s pupils dilate. “Obviously not, dork.” Dean pulled him closer, hands coming around his back. 

Letting himself indulge for a few moments, Castiel pulled back. “And hand jobs don’t count?” 

“No.” 

“What about blow jobs?” 

That gave Dean pause. “What?” 

“Dean.” 

Dean was flustered now. “I—I mean, we’ve already done that.” 

“If I blow you, would that count as a ‘first time’?” Castiel made the air quotes and everything. 

“Well… okay, we’ve never done that before…” 

“It’s the only thing I was ever really good at.” 

Dean made a squawk of protest. “Cas, don’t say that—“ 

“It’s not technically the penetration you meant.” Castiel winced internally at his word choice, hoping a new car wouldn't show up in the ridiculously long driveway after this. 

Dean swallowed noisily. “I…” 

Castiel smelled an easy victory. He pressed his chest close to Dean’s, reveling in the warmth coming off his skin. “I just want to make you feel good, Dean. You always take such good care of me, and I just want to make sure you get taken care of too. Please?” He looked up at Dean from under his lashes, knowing he was laying it on thick but also knowing it was working wonders on Dean’s self-control. 

“This isn’t fair.” Dean’s voice was several octaves higher than usual. His fingers were twisted in the comforter. Castiel walked his fingers up Dean’s arms, chuckling when the muscles jumped. He traced up to Dean’s collarbone, and up the column of his throat, ticking over the contours of his lovely face. 

“Shhhhh... I won’t do it if you don’t want me to…” he said, honestly. Earnestly. His voice dropped down to a whisper. “But I really, really want to blow you. I want to feel you get hard in my mouth and come all over my lips.” 

“Shit.” 

Castiel blinked innocently. “That doesn’t sound totally repulsive to you?” 

Dean shook his head, and kept shaking it, like he wasn’t sure what he was doing. “N-no, but Cas—“ 

“Dean, do you want me to blow you?” The tension was fizzling in the air between them. Castiel was going to get his mouth around this man, he could feel it. He just had to get Dean on the same page. 

Suddenly, strong fingers came up to clamp in his hair, dragging him back so Dean could look him square in the eye. _“Yes.”_

Castiel could feel his own cock jump at the permission. He quickly scooted down, throwing aside the blanket that Dean still had tucked up around him. He was bare underneath. Dean’s cock was already half-hard, and it was easily convinced to get to full mast very quickly as Castiel slipped his tongue in a dirty circle around the tip of his cock. Dean gasped, fingers tightening once before letting go deliberately. 

Castiel grabbed his hand again and pressed it firmly to the back of his head. He didn’t give this privilege to many clients—hardly any—but this was something he trusted Dean with implicitly. “Show me how you like it. Tell me how to make it good for you.” 

“Trust me, honey, I won’t take long.” Dean ground out. 

Smirking, Castiel decided to bring out the big guns and swallowed Dean down in one go. He was actually pretty decent at deepthroating, even if it sometimes made him lose his voice. It always made for great reactions from his clients when he brought this out. Dean was no disappointment. The second his cock hit the back of Castiel’s throat, Dean made a _guHUH_ sound and clutched at Castiel’s shoulder so hard that Castiel would have smiled if his mouth wasn’t full. 

It only took Dean about seven minutes to go from half-hard to ready to blow, something that made Castiel very proud. Even after all he’d been through, and the weeks he’d been spoiled here with Dean, he hadn’t lost his talent. Usually when he was giving head, he found it easy to tune out—just let the client get what they needed from his mouth and get paid. With Dean, he found himself fixated on every tick of his face. He adjusted technique when Dean’s face smoothed out, went harder when Dean’s face scrunched up and his fat cock twitched in his mouth. When Dean finally came, it was with one hand tangled in Castiel’s hair, and the other clutching Castiel’s hand for dear life. It was an almost laughable mirror of their first time together. 

Panting, Castiel pulled off and dropped himself on the pillow next to Dean. Next to him, Dean wasn’t in much better shape. He looked like he’d just gotten hit with a freight train. 

“So, was that okay? Did I live up to the—oof!” Castiel was suddenly pulled in close to Dean’s side, the both of them still extremely sweaty. 

Like lightning, Dean wrapped a hand around Castiel’s cock and laid a kiss on his mouth that made the room spin. For all that Castiel was feeling smug about making Dean come quickly, it had nothing on the minuscule time that Dean had Castiel spurting in his hand. Castiel blamed it on getting so worked up by watching Dean. 

“That was amazing,” Dean said, still breathless himself. “I love—I loved it.” 

Castiel tucked himself close to Dean again, firmly shutting his eyes as Dean draped himself over him once again. “Well… good.”

…

Really, their relationship didn't change much from the original contract, even with the addendum that Dean wanted more affection and “realness” from Castiel. They still kissed when they saw each other, still curled up in Dean’s bed or on the couch together, still worked in the garage together. The painting from Castiel’s freakout had been hung on the wall as a twistedly humorous attempt at talking about their problems. Dean had told Castiel why he was hesitant to take that final leap. Castiel opened up about his problems with the financial aid department at the Institute, and Dean promised to take care of it with annoyance in his eyes. Castiel was delightedly smug that the anger was not towards him. 

Castiel was making great progress on his gift for Dean. He had gotten the skin around each eye almost perfect. The only thing missing was the iris color. Dean was set on blue—“it’s gotta be your eyes, dude!”—but Castiel, thinking it was a bit narcissistic, was set on green. Their almost weekly playful argument about it went something like this:

“I can’t have my own eyes staring down at me every day, dude. That’s weird.” Dean would say, rolling his eyes. 

Castiel would stand with his hands on his hips, paint smudged across the bridge of his nose. “Well, I can’t let you have a huge painting of my eyes staring into the living room either. What if someone saw?”

“That’s the point of a painting, isn’t it?”

“Not when they’re the eyes of your hired escort, no.” Castiel had put himself at peace with his place in Dean’s life. Dean wanted him there, there was no mistake. 

Dean would always grin mischievously. “Kinda makes it feel like I’m some king with a secret relationship with a concubine.” He’d say, waggling his eyebrows. 

Castiel would snort and shake his head. “I’m not a concubine, and you’re not a king.” Castiel would gesture to whatever oil-stained outfit Dean would be wearing in the garage. 

Striding forward, Dean would slowly advance on Castiel, making him back up into his work bench. “Gonna be hard to remember that when I’m lookin’ at my favorite treasure.” Dean would press forward and capture Castiel’s mouth with his own. Castiel would surrender to his will in almost no time. 

Their argument never got solved. 

So the painting’s irises stayed blank for the most part. Castiel had outlined definition for the iris, lines that made it look like a nebula exploding within the depths of the eye. When he had taken an astronomy course in high school he had been fascinated by how similar a close up of the human eye looked to a photograph taken from the Orion Nebula. Art and science bound together. 

Dean worked continuously on whatever was under the sheet across the room. Castiel felt he had done a fantastic job of not looking underneath, as Dean had asked, though the curiosity was killing him. Whenever Castiel made a vague comment about it, Dean would raise his eyebrows and say something like “You’ll know soon enough, Cas.” or “It’s gonna be great, babe. You’re gonna love it.” 

Castiel just wished he knew what he was waiting for. 

Sam came around to visit now too. Dean had asked Castiel, one night when they were curled up in Dean’s bed, if he’d like to properly meet the younger Winchester brother. Castiel had been caught a bit unaware the last time Sam had come over, and genuinely wanted a chance to meet the brother Dean was so fond of. So now, not only did Sam and Castiel talk, they were fast friends, much to the chagrin of Dean. Castiel and Sam bonded over books, movies, and even (to Castiel’s unending delight and Dean’s confusion) their shared hatred of Paul Gaugín. 

“So you guys are good, then?” Sam asked one night after a movie marathon of the original Star Trek movies. “You seem… different since the last time I saw you.” He said to Dean.

Dean looked down to where Castiel was draped casually over his lap. Castiel shrugged. Dean looked back up at Sam. “Think so. We talked some stuff out. Think we’re in a better place.” 

Castiel nodded his agreement. He felt more stable in his relationship—and it was a big step for him to even call it a relationship—with Dean. He felt wanted and desired, even if it didn’t manifest itself how he wanted all the time. Dean stroked a hand through his hair, and Castiel fought back a shiver. No need to traumatize Sam with exactly how Dean’s affection for him did manifest. 

“Well, I still think it’s weird, but I’m happy for you.” Sam smiled at the two of them.

Dean waved a hand in the air, “Alright, don’t make it girlier than it has to be.” He made a face like he was in pain, but a smile lurked at the edges. “Speaking of being happy for other people, how goes the baby-makin’?” Dean waggled his eyebrows.

Rolling his eyes, Sam shook his head. “Dude, I think my dick’s about to fall off.” Dean burst out laughing. “No, seriously! Sarah practically jumps me every time I walk in the door, which like—I’m not exactly complaining—but if she doesn’t get pregnant soon… she might start to think the problem is with me.” Sam grinned crookedly, and suddenly Castiel could see how tired he looked. 

“You’re spending too much time at that law office. Startin’ to go impotent.” Dean said, earning him a throw pillow to the face. He cackled in response. 

The task of essentially being paid to date Dean Winchester also came with such trials as public dates. Castiel was used to his clientele favoring dark alleys and bathroom stalls for their transactions, preferring to stay as far away from prying eyes as possible. That Dean wanted to take him out and—practically—show him off was… new. 

Their first “real” outing was such a perfectly normal activity for a couple that it boggled Castiel’s mind a bit. They went for a walk around the city after lunch at a pizza joint. Sure, they had gone out together to get art supplies for Castiel, anyone could have seen them together. But they didn’t see what was happening now. They didn’t see Dean casually sling an arm around Castiel’s shoulders, pulling him in close to plant a kiss against his cheek when Castiel said something so deadpan that Dean couldn’t help but laugh. They didn’t see an amusedly exasperated Castiel tug Dean along the sidewalk by the hand when he got distracted by what was clearly a service dog in training in the window of a bakery. They certainly didn’t see him get pushed into a courtyard behind a church, or watch Dean sink down to his knees, or bear witness to the most public orgasm Castiel had ever had in broad daylight. On a Sunday no less. 

If it weren’t for the checks being handed to Castiel every week by Dean, Castiel might have fallen for the charade himself. For all intents and purposes, he and Dean acted like any other couple might. They leaned on each other waiting in line, they watched television in the living room, they even went to a Cubs game one sunny afternoon. It was perfect. 

Until it wasn’t. 

Their dinner started out perfectly normal. The venue was new, just opened last week. The owner was some baseball star recently moved back to the city, trying to keep his place in Chicago relevancy. The restaurant promised the best steaks, cooked by the finest chefs brought in special all the way from California. Dean had just wanted to see if the steak was as good as the one he’d had in Omaha the last time he was there on business. 

They had their reservation—Winchester for two—and were shown a table near the back. Photographers were everywhere, snapping pictures of the guests, the staff, the food, anything they could bring back to their editors to prove they’d been to the hottest opening in town. The maitre’d looked haggard by seven pm. Their server was friendly, though clearly ready for a break that wouldn't come anytime soon. The food was excellent. Castiel didn’t think twice when Dean leaned across the table and planted a kiss on his lips before taking another bite. 

“What’s the verdict on the steak?” 

Dean chewed for a minute, thoughtfully. “Not as tender as I would’ve liked. Certainly better than that other joint, Romero’s down the road.” 

“You like Romero’s.” Castiel said, huffing a laugh. 

“Not anymore, I don’t.” 

The server came by again, asking if they wanted to see a dessert menu. When Dean replied that they would, the server blinked at Dean, as if she were seeing him for the first time. “Hey, you’re Dean Winchester! You dated Bela Talbot from the fashion house!” 

Dean blinked, and smiled. Charming as ever. “Yeah, Bela’s been hard at work.” 

“Oh, I loved the spring collection last year—or was it two years…” she stopped babbling. “I’m so sorry, I’ll get you that menu.” 

When she left, Castiel raised an eyebrow and smirked across the table. “Bela Talbot, huh?” 

Dean’s face reddened. “Shut up, she has an accent.” 

“I heard she lives off of black coffee and raw almonds.” Castiel said, nibbling at a breadstick. 

Dean huffed and took a sip of wine. “Don’t forget the souls of the innocent.” 

When the server came back with the menu, Dean gave it a cursory glance before asking for the tiramisu and coffee. She smiled and made good on her promise to have it to their table in five minutes. With the plate in front of him and the fork in his hand, Castiel stopped and looked up at Dean. 

“I just want you to know how different we were raised.” 

“Wha’ d’you ‘ean?” Dean asked with his mouth full, crumbs falling from the corner of his mouth. 

Distractedly brushing them away, Castiel sighed. “I don’t think I’ve ever eaten so well as when I’m with you. I’ve never had tiramisu.” 

Dean swallowed. “Well, then open up sweetheart.” He scooped up a bit of tiramisu onto his fork and held it out to Castiel. “‘Cuz I’m takin’ care of you now.” 

Castiel obligingly opened his mouth, wrapping it around Dean’s fork, hanging onto his hand while he pulled off slowly. He savored the bite of dessert in his mouth, but not nearly as much as he savored the way Dean’s pupils dilated at the sight he made. Dean leaned forward urgently in his seat. “Better hurry up. I’m takin’ you home right after this.” 

Castiel licked his lips and smiled. 

…

When Castiel came to the next morning, swaddled in the thick comforter of Dean’s enormous bed, it was to the shrill sound of his cell phone going off at least seven times in succession. The chilly AC-cooled bedroom was enough to keep Dean close through the night, and he waved his hand vaguely in the direction of the sound as he groaned for Castiel to turn his damn phone off. Rolling over, Castiel thumbed it awake and immediately pressed the switch on the side to silence the ringer. He sighed, thirteen texts from Anna, and several missed phone calls from numbers he didn’t recognize. He pulled up the texts from Anna. 

_Um?????? Mind telling me why you’re all over the news?????  
Sent 7:02am_

_CASTIEL. YOU’RE ON THE TABLOIDS.  
Sent 7:12am_

_Can you just call me or something?  
Sent 7:15am_

_Look, I know I was going to be supportive here, but this is getting a little out of hand.  
Sent 7:20am_

_THERE ARE REPORTERS AT OUR DOOR. WHERE ARE YOU.  
Sent 7:33am _

Castiel sat bolt up in bed. Dean grunted from his side, stretching against Castiel’s thigh. “W’as goin’ on?” He asked sleepily. 

“Where’s your phone?” 

Dean frowned at the edge in his voice. “It’s over here. It’s off though.” 

“Turn it on.” Castiel feared the worst. 

“Okay, okay. Bossy.” Dean turned away, reaching for his cell. He lay back against the pillows, waiting for his phone to turn on. When the power screen cleared, Dean’s phone was also hit by more than a dozen texts and missed phone calls, turning his cell into a vibrating brick. He looked to Castiel with a questioning look, panic rising in his eyes. “Um, Cas? …did I miss something?” 

“I think we’re on the news.” 

“What? Why?” 

Castiel didn’t answer. Instead, he threw the covers off and bolted to the sitting area with the huge television, nearly tripping over the sheets. He scooped up the remote tablet and hurriedly pressed buttons, cursing when they didn’t do what he wanted. With a sigh, Dean came to stand beside him, far more calm than Castiel was, and pressed the power button, turning on the television to the news channel they had been watching the night before. 

A perky blonde reporter was standing in front of Winchester Holdings LLC. Castiel couldn't hear what she was saying, as he was distracted by the headline at the bottom of the screen. 

“Oh… shit.” Castiel said, running his hand through his hair, wrapping his arm around himself. 

“Yeah…” Dean echoed weakly, sinking down to the couch beneath them. 

Across the screen, in big white letters: WINCHESTER LLC CEO HIRES MALE ESCORT FOR ‘PRETTY WOMAN’ FANTASY.

**Notes for the Chapter:**

> My man Vonnegut once gave me some writing advice that boiled down to "make terrible things happen to your favorite characters." Buckle up, kids. I got plans. 
> 
> Thanks for reading!  
> -azo


	15. Don't Wanna Fight

**Summary for the Chapter:**

> Sometimes, reality hurts worse than fiction.

“Dean—“ Castiel started. He reached out towards the other man, without taking his eyes off the screen. The reporters had gotten inside the building, and someone—probably one of the newer receptionists—had let them upstairs to the main administrative offices. 

Dean’s eyes are glued to where the headlines roll across the bottom of the screen. The reporters don’t know much at this point, but what they do know is… incriminating. 

_CEO of Winchester Holdings LLC has allegedly been seeing the escort for a period of three months._

_Not much is known about the nature of their relationship at this time_

_Sources say the escort is known as Castiel Novak, a student at the Chicago Institute of Fine Arts_

_Winchester allegedly paid Novak for sexual acts and favors in exchange for his tuition money_

Castiel tried again, tearing his eyes away to brush his fingers against Dean’s shoulder. Dean stiffened at his touch, and Castiel recoiled. Instead, he pulled his hand back to his lap, curling it tightly around the other. He turned back to the screen and the two watched as the reporters methodically and casually break apart everything Dean had worked for in the last decade. 

They questioned everyone they saw. Most of the employees there on the weekend knew enough to keep their mouths shut and walk quickly past the perky blonde reporter and her dark haired partner, but this only made their grins wider. They knew they’d found a story, and they weren't leaving until they’re satisfied. 

What really drove a stake hard into Castiel’s heart was when they asked each other about the ethics of the scandal. 

“Winchester Holdings prides itself on doing the ethical thing in every case, right? Stand up for the little guy. How is this gonna look in front of an ethics court, do you think, Viv?” 

“Well, Brent, it’s sure not looking very good. Already, I’m getting reports of several huge partners pulling out of deals with Winchester. Isn’t that just tragic?” She answered, with an expression of absolute glee. 

On screen, the blonde one—Vivienne-something—turned and cornered a redheaded woman as she stepped off the elevators. The redhead had obviously just come back from getting coffee, evidenced by the cup in her hand and the confused look at the number of people in the hallway. 

“Oh fuck, Charlie.” Castiel heard Dean mutter beside him. 

“Miss, you work for Mr. Winchester, don’t you?" Vivienne started, thrusting a microphone in her face. 

Charlie frowned, “In a manner of speaking, I guess—“ 

“What can you tell us about Mr. Winchester and the escort he hired for the past three months?” 

Castiel jumped as Dean let out a triumphant holler, teeth clenched in a snarl. “You son of a bitch! Charlie doesn’t know anything! No one there does!” 

When Charlie told Vivienne as much, she was quickly pulled out of frame, especially as she started advancing on the camera crew and promising harm in explicit terms if they didn’t vacate the premises immediately. Dean snapped off the television with a growl and stood, nearly upsetting Castiel with the sudden weight shift on the couch. 

Dean walked over to the window and peered out the blinds. “Damn reporters at the gate already, too.” He reached out to either side of himself and wrenched the curtains shut. “We’re trapped in here like a goddamn castle raid.” 

Standing on shaky legs, Castiel walked over to the window to stand beside Dean. He hooked a finger around the heavy fabric of the curtain, tugging it aside to see the view of the front gate. Indeed, a swarm of reporters hovered in front of the gate, some even hanging off the gate itself, balancing their cameras as they try to hoist themselves over the metal. “Do you think they’ll get in?” 

Dean spared one glance out the gap in the curtain at the gate as one ballsy paparazzo landed with a thump on the gravel below. Suddenly, a gunshot sounded, startling Castiel. His eyes flickered across the lawn, and saw Bobby trudging across the lawn, shotgun in hand, yelling about trespassers and Ron Paul. “I don’t think that’s our biggest issue right now.” Dean said, smile spreading wryly across his face. Castiel couldn’t see Bobby’s face, but thought it must look murderous, from the way the reporters scrambled back up the gate and away from the angry man. 

“What are we going to do?” Castiel asked quietly, as Dean let the curtain fall, bathing the room in darkness. 

“I don’t know. I have to talk to Charlie and my advisory team. See how much of the damage we can control.” Dean let his fingers stroke along Castiel’s arm as he walked back to the bed. He pulled on his jeans from the previous day, forgoing his underwear. He turned around to face Castiel. “And they know your name,” he looked stricken. “I’m sorry you got dragged into this shit too. I never meant for anyone to find—“ Castiel crossed the room and pressed a hand over Dean’s mouth. Dean grabbed Castiel’s hand and moved it to his cheek. 

Castiel spoke, “Don’t worry about me right now. I’m a nobody, compared to you. They won’t care about me at all, other than the fact that you paid me.” 

Looking worried, Dean pressed a kiss to Castiel’s palm. “They’ll want to know everything about you.Your day job, where you live, where you grew up. Castiel, this is serious.” 

“Do you want me to go?” Castiel hoped against hope that Dean wouldn’t send him away. It would certainly be easier to. Dean could write the whole thing off as a mistake, say he met Castiel at a bar and only wanted a one-time thing. He might even be able to spin it in a way that sounded like Castiel had extorted the money, break any ties he had with Castiel to save his company’s reputation. Castiel could leave the city, leave the Institute, change his name. He didn’t really want to leave Dean, Mr. Guerrero, and the whole of Chicago behind… but he also couldn’t bear to see Dean humiliated. 

Dean tilted his head, speculative. “Do you want to leave?” 

“Not if I’m being honest, no.” Castiel gripped Dean’s hand a bit tighter. 

A mischievous twinkle lit Dean’s eye, ”Then do you want to go for a drive?” 

Castiel answered with a grin of his own. “Sure.” 

…

Once the angry groundskeeper had successfully chased everyone back outside the gate, Alfie was sure they’d run out of options. If they couldn’t get inside the Winchester Estate, and there was as little information at Winchester Holdings LLC as Bernard said, they were definitely going to get back to the station to an earful from their supervisor, Janine. For his first week at The Daily Grind, Alfie was having a hell of a time making friends. He thought living in Chicago would be different—more glamorous, maybe. More exciting. Instead, he was caught outside the mansion of a billionaire caught in a sex scandal. Probably an old dude, lost in a fantasy. 

Alfie looked around. The walls on either side of the gate were tall, with ivy climbing up. He’d read somewhere that ivy actually destroyed the stonework, even though it looked cool and historic and whatever other shit the layout mooks went on about while designing photoshoots. “Capture the architecture, Alfie!” “We need more of the Gothic influence, Alfie!” God. Alfie was tired of hearing it. Maybe if they waited around long enough, the ivy would crumble the wall and they could get into the estate without the psycho with the shotgun coming after them. Alfie fiddled with the lens cap and wandered away from the group. 

A small clearing in the bushes afforded him some space to think, away from the bodies and swearing of the frustrated journalists. Poking around, he noticed a chunk cut out of the brick, a foot or so up from the ground. Glancing back to the group, Alfie slung his camera over his shoulder. He put his hands on the wall above the divot, and placed his foot on the cut out. Hoisting himself up, he found he could get his hands up to the top of the wall. Hanging off the top, he found another divot a few feet above the first one. This was great! Maybe he could sneak in over the side, away from the scary gardener and just… show up at Winchester’s back door? Okay, he wasn’t real clear on the details yet, but at least he had a leg up over the rest of the yahoos at the gate… no pun intended. 

Alfie heaved himself over the wall, just in time to hear an engine revving from somewhere unseen. He glanced back at the road, thinking one of the reporters had gotten fed up with the nonsense and left in a huff. The revving got closer, causing Alfie to whip his head around towards the house. He saw a streak of black fly towards the gate. The unmistakable sound of metal hitting metal, followed by the squeal of twenty-five men and women as they dove out of the way of the black car smashing through the gate. Definitely not an old dude driving. Some of the reporters tripped over themselves or each other in their hurry to get out of the way of the speeding vehicle, while others sat back where they had fallen on their ass and snapped pictures as fast as their shaking fingers would allow. A delighted whoop sounded from the car, audible even from where Alfie was perched. Ted Nugent’s Stranglehold was cranked up even louder from inside the vehicle, as the car fishtailed around the curve and sped out of sight. A shocked murmuring was left in the wake of the car—Winchester’s no doubt—along with an impressive cloud of dust, causing the reporters to hurriedly cover their cameras with whatever they could find. 

When the dust cleared, the group of reporters glanced uneasily back at the opening of the gate at the sound of a shotgun being cocked. The gardener, or groudskeeper, or fucking arms dealer as far as Alfie was concerned, stood in front of the group, baseball cap set low on his face, and a chilling expression firmly in place. 

“You idjits got ten seconds before I accidentally lose my grip on this trigger.” 

Alfie jumped off the wall, scooped up his camera, and ran ahead to beat Bernard back to the truck, parked at the base of the hill. He heard the rest of the group hot on his heels. Maybe he needed to consider a new career. 

…

Castiel wasn’t exactly sure where they were. They definitely weren’t in the city limits; they’d driven for over an hour west. They were practically out of the suburbs surrounding Chicago, parked up on a hill overlooking a small lake with a park nearby. They’d grabbed Burger King on the way out of town and were sharing a large order of fries between them. Dean moved his sunglasses to the top of his head, squinting in the afternoon sun until he moved the sun shade down. 

“Do you think I hit any of them?” Dean asked, the first words spoken between them since they left the house. 

Castiel shrugged. “How much do you really care?” 

Dean nodded thoughtfully. “Bobby will take care of the rest of those ass clowns anyway.” 

Chuckling, Castiel popped a fry in his mouth. “I don’t know if I’ve ever seen Bobby look so happy with a gun in his hand.” 

“I think he misses when he had to keep the coyotes off his farmland back in Kansas.” 

Silence fell between them again as their laughter died out. “Dean, what are we going to do?” He hoped Dean knew he meant beyond today’s craziness. They couldn’t stay out here in the suburbs forever, and they certainly couldn't hide from the media. 

“I don’t know, Cas. I don’t think I’m ready to face the music just yet, but I gotta. I have to go deal with the shit show those paparazzos have cooked up, and I can’t let my company suffer because of this.” 

Castiel nodded. “I understand. I’m sorry this is such a mess. I should have been more careful, I should have kept a lower profile.” He put his head in his hands, dejectedly. 

“You know this isn’t your fault, right?” Dean said, nudging Castiel’s arm. “I just can’t keep my hands off you, even at that restaurant. That’s our problem.” Dean stretched across the back of the seat, putting his arm around Castiel’s shoulders and tugging him close. 

“I just feel like we should have seen this coming.” Castiel sank into Dean’s warmth. He took off the sunglasses Dean had lent him and put them on the dash. 

He felt Dean shift as he shrugged. “Probably would have happened sooner than later.” Dean chuckled. “Feels kinda illicit, though, doesn’t it? Sneaking around from the press.” 

“Well, I’m glad you’re getting some kind of amusement out of this.” Castiel said, feeling barbish. 

“Oh come on, busting out of gates in a car, cruising around town with a billionaire you’re secretly banging. Isn’t this every teenage fantasy you’ve ever had?” 

Castiel rolled his eyes. “You just want everything to be like a movie.” 

“I’ve got my phone. We can make a movie if you like…” Castiel didn’t have to pull away to see Dean waggling his eyebrows. 

“If you wanted to have sex in your car, you only had to ask.” 

“Honey, I’m askin’.” 

Castiel huffed a laugh and pulled away, turning to swing his leg over Dean’s lap. He took a second to run his hands through Dean’s hair, getting a good enough grip to pull Dean’s head back a bit, exposing the long line of his throat. “You think you’re such a rockstar,” he said softly, delighting in the way Dean’s throat worked around a swallow, lust in his eyes. He bent forward and sealed his mouth against Dean’s clavicle, nibbling the skin and sucking until a mark was sure to rise to the surface. Dean’s hands came to clamp around his hips, pulling Castiel into a delicious grind against himself. 

“God, I really hope some nosey cops wander up here. Really give ‘em a show.” Dean panted into Castiel’s hair. 

“Can’t help it. I love your throat.” 

“Did you hear me complaining? Shit, baby, right there—” Dean was cut off by his own breath being robbed by Castiel pressing his lips to Dean’s. With a hand on either side of Dean’s face, Castiel tried to pull himself into Dean’s very being. He pressed himself as close as he could to the man beneath him. Dean thrust up, pressing his hard cock right against Castiel’s. They both released twin groans at the contact. 

Castiel reached down and took hold of Dean’s wrists, where his hands were still clamped around Castiel’s hips. He pressed Dean’s wrists into the leather seat, pinning him in place, totally at Castiel’s mercy. 

“Let me fuck you.” Dean panted. 

Drawing back a bit, Castiel stared. “Seriously? You’re ready?” 

“You remember what I said?” Dean’s eyes were wide and almost manic, “About how your first time should be with someone who cared about you? Someone who could love you?” 

Castiel’s breath caught. “Yes—I… Dean—really?” 

Dean swallowed noisily, and stared back, equal parts terrified and certain. “Absolutely.” 

“I just—Dean, me too.” Castiel stared at the man beneath him for a moment longer, before pressing his mouth solidly to Dean’s. 

“Then come on, let’s do this. Please, baby. If you’re ready, I’m ready.” Dean pleaded with him between kisses. Castiel felt a grin creep across his face. 

Finally.

Castiel worked the zipper of his own jeans down, and was working diligently on Dean’s. When he released Dean's cock, he took extra care in making sure he was all the way hard. Dean’s shaft was hot in his hands, fluid from the head slicking his way. When Castiel added a slight twist in his stroke, Dean let loose a litany of soft noises, ones Castiel drank in like water in the desert. 

The ringing sounded muffled from its place in the pocket of Castiel’s jeans, where they were crumpled on the seat. The vibration of the ringer caused it to slide out of the pocket into plain sight on the bench seat. Castiel couldn't help but glance at the screen to see who was interrupting the most important sexual encounter of his life, and the sight of the caller ID caused his blood to run cold. It was a saved number, one that he rarely used, but dreaded when it came up. 

_Institute Admin. Dept._

He pulled away from Dean’s mouth with a smack that would have been comical in any other situation. Dean looked positively wrecked, eyes heavy lidded and lips swollen, as he blinked in confusion at the sudden lack of weight in his lap. 

Castiel shuffled ungainly as he struggled to reach the phone and get himself situated enough to answer. 

“This is Castiel.” 

“Mr. Novak, this is Dr. Johnson from the administration center for the Chicago Institute of Fine Arts, are you busy?” 

“No, I guess not— is everything okay?” 

“Well, that’s the issue, I’m afraid. We recently got wind of some of your… extracurricular activities with one Mr. Winchester, a prominent member of society.” 

Castiel felt all the blood leave his face. “I—but…” 

“You understand we can’t afford to have that kind of… attention focused on the Institute, especially before the Gala at the end of the semester.” 

He understood. Castiel understood perfectly well. The Graduate Gala was the one event that pulled in 70% of the funding for the next year. Students about to graduate, as well as alumni, put in pieces to be auctioned off. Only the best were chosen for auction, and it was a huge honor to even be featured. Castiel had been considering putting in his painting of eyes meant for Dean’s living room, just for the honor. “So, what does that mean?” 

“I’m afraid that we have to… terminate your place here at the Institute. Cut ties, as it were.” 

“You're making me leave?” Castiel clutched the phone as tight as he could, trying to hold on to some scrap of dignity. Dean’s head whipped around, his expression one of mixed panic and horror. Castiel turned away when Dean reached for him, not able to face this quite yet. 

“It’s unfortunate, yes. We really feel that we have no other choice. I’m terribly sorry, Mr. Novak. Of course, you will be refunded whatever portion of this upcoming semester’s tuition you have already paid—“ The voice on the end of the phone faded into a buzz as Castiel zoned out. He must have ended the call and put the phone down in his lap. The next thing he was aware of was how he jumped when Dean brushed his fingers over his arm, silently asking permission to touch him. 

“They’re kicking me out.” He said tonelessly. He was dimly aware of the fact that his pants were still hanging open. Dean had zipped himself back up, apparently not hard anymore. Figures. Castiel managed to fuck this up once again. 

Dean’s hands fluttered, not knowing where they were allowed to touch. “Cas—I don’t… I can’t… how do I fix this—?” 

Castiel turned away to face the window. “Can we go?” 

Nodding furiously, Dean reached out again. “Sure, we can head back home and—“ 

Castiel moved out of his reach. “I’d like to go back to my apartment. I need to stop by your house to grab some things, but… I’d like to go.” 

Dean hesitated a moment, before turning back in the driver’s seat and starting the car, turning around to back the car out from the lookout point. He got the car back on the main road, and headed back towards the city. 

…

When the car rolled to a stop in Dean’s spacious garage. 

“Castiel, I am so sorry.” Dean said. He flexed his hands on the wheel, leather creaking under his fingers. 

Shaking his head, Castiel turned to the door. “I just need to grab my bag from upstairs, and then can you take me home?” 

Dean snorted, humorlessly. “I might feel better about that if I was sure I was going to see you again after that.” 

Sighing, Castiel shrugged. “I’ll see you in a few days, alright? I just… need some time.” 

He opened the car door, and got a foot outside to the ground. “Maybe, it would be easier,” Dean started, not looking at Castiel, “if we stopped this altogether?” 

“What?” 

Dean looked down at this lap, where his hands were turning his keys over and over. “Think about it, if I’m out of the picture, you can move on. Get out of town, go to a new art academy, start over?” 

Castiel stared at him incredulously. “How am I supposed to go anywhere? In case you hadn’t noticed, my lack of money was the reason I started this whole thing." He knew his words would sting, but he couldn’t help it. 

“I’ll help you. I can pay for everything, that’s fine. I’ll still hold up my end of the bargain, and… there’s a car you can use.” 

Feeling tears gathering, Castiel spat out, “You’d give me one of your cars? That’s how bad you want me out of your life?” 

“No! Cas—baby, never…! I just… I’ve been fixing one up for you and I meant to give it to you—well, it doesn’t matter. But it’s there if you want it. I’ll give you money. Whatever you want.” 

Castiel’s worst fears were being realized right before his eyes. Dean didn’t want him anymore. Didn’t want to deal with the hassle of the drama he brought with him wherever he went. Dean wanted him gone so bad, he was willing to pay him to get out of town as fast as he could. 

“As long as I leave.” 

Hesitation, and then, “Yes.” 

“Fine.” 

Incredulous now. Like he didn’t believe Castiel would take the bait. “What?” 

“I’ll go. There’s nothing left here for me anyway.” 

“Cas—“ 

“You want me gone so bad, don’t you? Want this all to be over?” 

“Castiel, wait—“ Dean put out his hands again, reaching for Castiel’s hand. 

Turning away, he spoke through angry tears now, unable to stop them. “Easier if the hired whore just disappears, right? Where’s the car?” 

Wordlessly, Dean reaches across Castiel’s lap and opens the glove compartment. He pulls out a set of keys and hands them to Castiel. Wrenching open the car door, Castiel storms out and across the garage to where the canvas-covered mass sat, still undisturbed since the last time they were down here. 

He ripped the cover off, and barely spared a glance at the sapphire-blue paint job of the expertly restored roadster, before hauling himself inside. He jammed the key in the ignition and turned the engine over. He looked over his shoulder to throw the car in reverse and back out of this stupidly big garage. He pointedly ignored Dean, leaning against the Impala, and his carefully blank expression. 

Castiel whipped out of the garage as fast as he could, turning onto the main driveway. He sped towards the gate, not able to look in the rearview mirror, forgetting his bag, trying desperately to forget the man in the lakeside mansion he was leaving behind. Dean didn't love him, no matter what he said. The best he could do was chalk the encounter up to a learning experience and move on. It was one of the rules, after all. 

Never fall in love with the client.

**Notes for the Chapter:**

> Sorry. 
> 
> -azo


	16. Two Sides of the Same Coin

**Summary for the Chapter:**

> Aftermath of decisions, both sides.

Castiel felt numb. 

He flew past the gates, determinedly not looking at the haggard-looking reporter still nosing around at the gates—curious, but still with enough memory of Bobby to stay a safe distance from the gate itself. He whipped onto the main road and dodged the ever-heavy Chicago traffic on the main highway out of town. He was not sure how he managed without hitting anyone else. He wondered if he would care if he did. 

He vaguely registered turning south on I-57, heading out of the city. The radio was not on, and Castiel did not try to fill the silence. The car itself was well-built. The suspension was solid and did not pick up any of the roughness of the road. Built by strong hands. Castiel forced his train of thought away, so as not to lose control this close to the city. He had to go. 

Reasonably, Castiel knew that it must take about 45 minutes to leave the city on I-57, but it felt like only a handful of minutes before he was pulling west on I-80. 

Where would he go? 

Certainly, Pontiac was an option. It was a terrible option, but it was there. He didn’t know how much of a life he’d have there if he went back. Then again, he also didn’t know how much of a life he was leaving behind. 

Castiel pondered this all the way to the first truck stop he encountered. When he stopped the car in front of the convenience store, he gave himself a moment to think. What was he supposed to do? What was expected of him? He didn’t have a job anymore, or any way to finish his degree. He also didn’t have any friends. He’d left everyone behind—Dean, Sam, everyone at the Institute… Anna—fuck. 

He whipped his cell phone out of his pocket and thumbed through until he could get to Anna’s contact page, thankful he’d had the presence of mind to charge the phone last night. He pressed Call and held the phone up to his ear, not sure if he could speak. 

“Cas! Thank God you called. Are you okay?" At the sound of her voice, Castiel found himself heaving for air. The familiarity was too much. He remembered when he’d come home from school after a bad day, and try to hold things together in the kitchen while he putzed around, waiting to be excused upstairs to his room. Everything would crash and burn when his mother would ask in her concerned tone, ‘what’s wrong?’ He hated that it was a similar effect with his best friend. 

“Anna…” Castiel started shakily, but found he could go no further. 

“Did he hurt you? Where are you?” 

“I—“ Tears started leaking, blurring his vision. He tried to push his voice out to be heard. Why couldn’t he just grow up and handle this like an adult? 

The line was silent for a moment or two. “Okay, bad question then, I’m sorry. Let’s start easy. Are you safe?” 

“Yes.” One word answers were about all that Castiel could vocalize right now, and Castiel was thankful that Anna could sense that. 

“Are you at his house or somewhere else?” Anna sounded calm and soothing, shushing him gently when his sobs racked over the phone. 

“‘Else. Gas station. Interstate.” Anna told him to look around and describe what he saw to her. He thought it was ridiculous, but focused in on the mural painted on the side of the car wash attached to the store. 

“It’s—a… a donut box. Big circles—all colors… it’s—well, maybe it’s not all donuts…” 

Anna asked a question here and there. Some made sense, like the name of the store and what major roads were nearby, but some were illogical: what color does the mural use most of? how would you describe the shapes? 

As he focused more on describing, he found he was able to string more words of a sentence together. He wasn’t sure for how long he was talking—he couldn’t put together enough focus for time—but Anna kept listening and asking questions when he slowed down. 

“—but not as many circles as the turquoise one… Anna, there’s only so much I can talk about, it’s a gas station mural. Why am I doing this?” 

“Because I’m almost fifteen minutes out from where you are, so if you keep talking to me, that’s less time you have to fight your own head, dummy.” 

Castiel huffed, incredulously, swinging around to see if he could spot Anna before she got here. “How’d you get here so fast? Trains don’t come out this far.”

“Jo at work owes me a favor—don’t look at me like that, keep driving!” She added, receiver muffled like she was talking to the person in the car next to her. Castiel had to smile through the tears, still coming down. Trust Anna to have his back, even when he hadn’t been around to have hers the past few weeks. 

“Thank you for coming to get me.” 

Castiel could hear her frown over the phone. “'A course I came to get you, stupid. You’re my best friend.” Silence then. “Do you think you’re going to come home?” 

Anna thought home was with her in their crappy apartment. Even when Castiel had been staying over at Dean’s more often than not, ‘home’ was there with their not-table and fuzzy television. 

“I don’t know if I can.” Castiel’s voice dropped down to a whisper. “They kicked me out, Anna. The Institute told me I can’t be associated with them. They found out.” 

Castiel knew that Anna didn't know the extent to what the Institute would have found out—he doubted the news got much right. But if Anna had known before he did that morning about everything, she was bound to have read more information trying to get the whole story. 

“We'll figure it out, okay? Together. It’ll be okay.” Anna sounded sure. 

Castiel bit his lip. “I’m gonna hang up and grab a soda or something. I need to walk around. You want a Coke or anything?” 

Anna paused at the sudden dismissal. “Vanilla if they have it. I’ll see you in ten minutes, Castiel. Promise.”

Castiel bid her farewell, and pocketed his phone. Scrounging through his pockets, he pulled out three dollars in change and bills. He glanced over at the glove compartment. Curiosity got the better of him and he leaned over to pop the latch. Inside was a number of items: a sealed envelope, a stack of hundreds bundled together, a flashlight, a new tire pressure gauge with instruction manual, and two packages of HotHands. All were items one might need if they were leaving on a long road trip to places unknown. 

Dean had always meant for him to leave. 

Grabbing the cash, he slammed the glove compartment shut, sure he dented the packaging on the tire gauge with the force of it. Dean wanted him gone so badly, he’d essentially packed a getaway car in case Castiel would have to be sent out in the middle of the night. 

Least he could do was buy Castiel and Anna a Coke. Vanilla if they had it. 

Castiel stomped out of the car, and swaggered into the store. The clerk at the desk was a greasy-looking man. Bald with a black mustache and a belly hanging over his carpenter jeans. He eyed Castiel appreciatively as he walked in—a look that Castiel recognized immediately, and Castiel knew he must look like a sight. His hair all rucked up from both Dean’s hands and his own, red marks on his neck, clothing all askew from driving. He probably looked like he just got done sucking off some dude in the bathroom. The clerk—Randy—called out a friendly “Afternoon!” as he entered. Castiel gave a polite smile in return as he found the soda section in the back. Randy would have been Castiel’s type down to a T a few months ago: available, desperate, and interested. Okay, so he hadn’t had very high standards. Fifteen minutes and twenty bucks later, though, and Castiel wouldn’t have cared. Castiel selected a Vanilla Coke for Anna, and a Sprite for himself. He took both to the counter and set them down, along with his three dollars. 

Randy punched in buttons on the register, and tried to make conversation. “So, you from around here?” 

Castiel had to hand it to the guy, he was doing much better already than some dudes he’d met on the street. “Yeah, just from the city. Around Boystown—sorry, Lake View.” Castiel wasn’t from anywhere near there, but he perversely liked the glitter that entered the man’s eye at that. 

“You headed somewhere?” 

Castiel smirked and nodded. He knew enough about himself to know that he wasn’t interested in Randy. He didn’t even feel up to pretending to be interested. How could he offer this man anything when he felt a shudder at the very thought of being with anyone. Still, flirting was a reflex. 

The man visibly flushed. “S-so, listen… I—uh. I—“ 

“Castiel!” A voice interrupted from the door. Castiel turned, half grateful, and saw a flash of red hair before he was attacked around the middle by Anna launching herself at him. Randy hurriedly gave him his change and scooted the sodas a bit closer to the edge of the counter, standing back. 

Castiel threw one last smile, hopefully apologetic, towards Randy before he followed Anna out to the car, handing her the Vanilla Coke. 

Outside, an attractive blonde was leaning against a beat up red Ford. Anna dragged him over to her and introduced her as Jo, her coworker from the club. 

Her grip was firm when she shook Castiel’s hand. “Anna said not to mention anything from the news, but I just want you to know that you shouldn’t take the media seriously. They twist anything out proportion.” 

Castiel smiled uneasily at her, while Anna jabbed her. “Not what he needs to hear right now.” Jo shrugged in response, pulling her phone out of her pocket and typing furiously. Anna turned to him. “What do you want to do?” 

“I don’t know,” he said honestly. “I don’t know if I can stay here. There’s nothing left for me here. But I don’t know what I'd do instead.” 

Anna shrugged. “Let’s leave.” 

Castiel stared. “And go where?” 

“Who cares? Let’s go to Los Angeles. Or Florida. Or Texas. Anywhere, really!” 

“My mom knows folks in Omaha.” Jo mentioned, offhand. 

“Omaha has a cool underground scene, and there’s an art scene too. It’s not as big as Chicago’s. Of course, there’s also New York if we’re really aiming for the stars here. And it’s not like rent would be too much—“ 

Castiel shook his head. “Anna! I can’t just ask you to pick up and move because I lost my job." 

“It’s not asking if I’m the one suggesting it. And Castiel… don’t take this the wrong way, but I think this stopped being just a job a while ago. This is more serious.” Castiel turned away from the pity in Anna’s eyes. 

He took a few steps away from the car. Was it really that easy? Just walk away and start over? There were billionaires everywhere, if you knew where to look. Art schools in more places. Wasn't that the great thing about being an artist? Always new places to paint or study. Visiting artists did it all the time. Places that could blow the Institute out of the water. He didn’t have to hate his life, turning tricks on the street. He could paint and have a normal job. Maybe even have some fun while doing it. Not for pay, if he didn’t want it. 

He turned back toward Anna. “And you want to go too? Just find a new city and start over?” 

Anna nodded and smiled. “It’s not like we’ve had a heck of a lot of luck here, have we?” 

Castiel had to hand it to her, their time in Chicago had been hard from the start. The past few months notwithstanding. Maybe what he needed was a clean break. Find some new men, music, color, inspiration, life, everything… somewhere else. 

“How do we pick?” 

Anna shrugged. “Depends. How’d you get out here?” Castiel gestured to the blue car, sparkling dimly in the afternoon sun. She stared. “Please tell me you didn’t commit grand theft auto before you high tailed it out here?” Jo looked up and raised an eyebrow, quickly going back to her phone, somehow typing even faster. 

“No,” Castiel said gruffly. “It was a present. Of sorts.” 

Anna looked like she wanted to say something, but she instead chose to say, “That means you’re driving, then. You need anything from the apartment?” 

Castiel shook his head. “Don’t you, though?” 

Shaking her head, Anna went back to the red Ford that belonged to Jo and pulled a duffle bag out of the back. “I wasn’t sure what kind of state you’d be in, so I packed the essentials in case we had to get out of town for a few days.” She grinned guiltily. 

Castiel embraced Anna tightly, before taking her bag from her and tossing it in the small backseat of the roadster. 

Anna turned and pulled Jo in for a hug as well. “Thanks for everything, Jo. I’ll call you when we get to—“ Jo cut her off.

“I don’t need to know where you’re going. Just be safe,” she hugged Anna back. “And Castiel—“ Castiel paused getting in the driver’s side. “Really, let things blow over. It won’t be like this forever.” 

Castiel nodded stiffly and waved, getting into the seat. Anna slid in beside him and buckled up. She glanced over and smiled at Castiel as he started up the engine. Here, away from the garage, he had a second to appreciate the pleasant rumbling sound as it turned over. He pulled out of the space, sparing one last glance at Randy inside, before waving to Jo and peeling out of the lot and back onto I-80 Westbound. 

Behind them, Jo got back in her piece-of-crap car and thumbed a few more words in her text. 

_— If you want him back, you’re gonna have to do some serious groveling._

She sent the message and started up her own car, taking a few tries to turn the engine over. Once in started, she pulled back onto the interstate and headed the opposite direction as the little blue car that used to sit in her uncle’s junkyard. 

… 

Dean knew that Missouri had to be worried. He’d stormed up to the kitchen and started pulling bowls and spoons out of the cupboard with no apparent rhyme or reason, and without saying a word to anyone. He rifled around in the fridge, hunting up eggs, milk, and some of that good vanilla. Missouri kept trying to edge in and get in his line of sight, at least to see where his head was, but he kept his head down and turned away. 

He sighed in relief when she scurried out of the room, probably to go gossip about him with Bobby. He didn’t know if he could speak, but he also didn’t want to hurt her feelings. 

Just another thing to add to his already awesome day. He dug a plastic measuring cup deep into the crock of flour, white with delicate blue printing. A gift from John to Mary in their first house, almost laughable in its simplicity in their estate. John was the newcomer to the wealth and scrutiny; a poor soldier returned to the Kansas countryside after the war, trying to make an honest living at the garage. Mary’s family was ridiculously wealthy, on vacation through the Midwest from her native New York state. They met and fell in love on the same hot July day. John was swept up into her world and family—mistrusting at first at his intentions, but warming up after a while after he’d proved his loyalty to Mary. 

Dean had always hated the press. Hated that they stuck their nose in places it didn’t belong, hated that they acted offended when they weren’t invited to company parties and events, hated that they all called him by his first name like they were old pals. He remembered one time his father reduced to nearly decking a rather insouciant member of the press right when Dean was about fourteen. He’d just come out as bisexual to his family and had started hanging around with a boy from school—Alex. He and Alex did everything together, both in school and out. Dean thought he was in love—and the press thought they’d start a family scandal. On their way to dinner one night, the press member tried to corner Dean into an impromptu interview outside a steak joint in downtown Manhattan. He’d been overly nosy, asking Dean how his family felt about the match. How they felt knowing Dean was out and proud. Were they happy? Were they disappointed? How would his mother have reacted? How the press had found out about he and Alex, he still hadn’t worked out past one of those things that the press magically seemed to find out about. Dean hadn’t had the words to explain it. He was flustered, embarrassed, and more than a little scared. He’d never seen his father push someone else before, not outside of play, but the way the reporter went sprawling to the ground, chasing his camera, told Dean that this was no ordinary altercation. Dean had been hurried into the car with their driver and younger brother. A short squabble outside of the car prompted Sam to ask what was going on, but their driver, Blake, assured the boys it was probably nothing and that Mr. Winchester would handle it. When John returned to the car, he told Blake to drive and to “mow down anyone who gets in your way.” After a moment, he turned to the backseat, where his boys sat. He said, “You don’t give those leeches an ounce of your time if you don’t want to give it. They’ve bothered me my entire life, they drove your mother mad. Don’t—“ he broke off. “Just walk away from them.” Sam and Dean had nodded dutifully, like good sons. 

That night, Dean told Alex they couldn’t hang out in public anymore. 

Alex was nice about it. He understood. Something about that interaction broke Dean up more inside than if he’d have yelled. 

Castiel would have yelled. He was bratty, hotheaded, spirited when he thought he could get away with it, and never anything less than exactly himself—even when he thought he had to put on a show. Dean loved it to pieces about him, and could have punched something when Castiel took Dean’s offer to leave so quickly and without a fight. He didn’t want to send Castiel away. It was the last thing he wanted. He wanted to bundle Castiel up in his house, make a nest with the softest blankets he owned, and tune out the news, the cameras, every prying eye that told Castiel he was rough trade, or not worth his place at Dean’s side. Because they were wrong. They were all wrong. Dean knew he’d drag Castiel down with his shit. He’d known it from the very start. He took a perfectly good kid—maybe a little rough around the edges from a few too many tough-but-necessary choices—and broke his heart and stole his future. 

And Dean knew he’d broke Castiel’s heart. He could see it all over Castiel’s face, as plain as if he’d written it there. Heard it in his voice, let slip through one word—“Fine.”—as he’d demanded to be let go. 

Dean glanced down as he stirred too hard, nearly knocking the mixing bowl over on its side. He relaxed his hand, sending the bowl clattering back into place. He hastily wiped at his eyes, glancing around, though he knew Missouri and Bobby would recognize his black mood well enough to give him a wide berth. 

He pushed away from the counter, moving to stand at the window. The gate was out of sight beyond the hill that was his driveway. He hadn’t seen any reporters on their way back in the estate, but he hadn’t really been looking. He’d been more concerned with what was about to happen and what he was about to say. 

Dean didn’t think he’d ever forget the betrayed look on Castiel’s face, even as he tried to hide it. 

_“That’s how bad you want me out of your life?”_

He closed his eyes. In his pocket, his phone belted out the chorus to a rock song that the caller definitely hated and was 100% the reason Dean chose it for their ringtone. He reached in his pocket and held his phone up to his ear. 

“Sam.” His voice sounded forced and unnatural. 

“Dean,” Sam replied. “Dude, it’s all over the news, are you okay? Is Cas okay? Where are you guys?” 

Dean swallowed, the feeling of his heart in his throat. “He left, Sam. I—I made him leave. He’s gone.” 

“Gone, where? Why would you do that, I thought you kinda liked the dude.” 

“I do. I did. They…” Dean rubbed his temple. “They kicked him out of the art school, man. It’s all my fault. I didn’t know what else to do.” He wanted Sam to yell. Wanted him to call him an idiot and a fool and everything else he knew damn well he was. 

Sam didn't yell. Didn’t get angry. Didn’t even sigh at his idiot brother. “Let’s find him and see if we can talk things over, okay?” Sam said. 

Rolling his eyes, even through the hot press of tears, Dean said. “He’s not gonna want to talk to me, even if I knew where he was. I gave him a car and he tore out of the garage like Vin Diesel outta a burning building. He won’t give me the time of day, he’s so mad at me.” 

Sam paused on the line for a moment. “Can I come over? We can go to dinner and you can tell me all about it?” Dean was silent. “Or we can not talk about it. That’s fine too.” 

A beep sounded from his phone, letting him know he had a text. Great. Someone else asking to be audience to his private life. 

“Yeah, Sammy. You can come over. We'll watch Ferris Bueller.” 

It was a tribute to Sam’s commitment to helping his brother that he didn’t complain like he usually did about Dean’s favorite movie. 

When he hung up with Sam, promising to see him in half an hour or so, his unread text flashed on the screen. He blinked as he read the name again. Jo hadn’t texted him in ages. She moved out of Ellen’s apartment above the Roadhouse a few years ago, wanting to make her own way in the city. She hadn’t accepted money from either Ellen or Dean, claiming she didn’t need anyone’s charity. It spoke to how long Dean had gone without having a proper conversation with Ellen that he wasn’t really sure what she was up to nowadays. 

_— Mind telling me why I’m going with my coworker to go pick up her roommate off the interstate, who also happens to be the Julia Roberts to your Richard Gere?_

Dean reread the message. And read it again. And once more for good measure. He tapped on the message, bringing up the reply screen. 

_ <<Sent  
You’re picking up Castiel? _

_ >>Incoming  
Looks like it, cowboy. Anna says he’s a wreck at some gas station off I-80. She’s bringing clothes in case he won’t come home. Can I ask what you did? _

_< <Sent  
I’d rather you didn’t. Helluva conversation starter after two years of radio silence Joanna Beth… _

_> >Incoming  
Can it, Winchester. I'm cleaning up your mess. _

Dean didn’t respond to that, taking his phone and himself away from the window. How had the universe aligned so perfectly as to put someone he knew in contact with Cas? This was perfect, this was going to solve everything, this was— 

—this could make everything a hundred times worse. If Castiel knew Dean had tracker dogs on his scent, it could drive him away even further. It was beyond creepy to be keeping tabs on someone who didn’t even know the connections he had. He didn’t know whether to press Jo for details or not. 

The decision was made for him, some twenty minutes later. Dean was pacing in his living room, trying to puzzle out what was the best course of action. He tried to slow himself down when his phone notified him of a new text, but fumbled for his phone as fast as he could. 

_ >>Incoming  
Anna’s inside. There’s a car here that looks just like that dump in your garage. But like. New. _

Dean wondered how long it would take for Cas to dump the car. Privately, he hoped Cas abandoned the car before he could read the letter in the glove compartment. He’d hoped to get that out before handing the keys to Castiel. Or giving the letter to him personally in a different, happier timeline. 

_ >>Incoming  
He looks like a train hit him, upon initial inspection. And that’s putting it mildly. _

Dean’s heart sank. He really fucked up. Another text. 

_ >>Incoming  
They’re talking about going away somewhere. Not Chicago. _

Somewhere not Chicago. Somewhere far away from Dean and all the trouble he’d caused, both intentionally and accidentally. It hurt like hell to think about, but Dean knew it was the best course of action for Castiel to get a clean break. He could start over. A new art school, new job. 

Maybe even a new someone. 

He pulled out his phone and thumbed a reply to Jo, taking a few times to get the right wording. 

_ <<Sent  
I think I need to let him go. really fucked up and he’s not going to talk to me, let alone let me apologize. _

_ >>Incoming  
YOU GAVE HIM THE ROADSTER. DEAN, YOU LOVE THAT PIECE OF JUNK. _

_> >Incoming  
You’re a fucking idiot in love, you know that? _

_< <Sent  
He's better off without me. _

Dean forced himself to type every letter of that text. Jo responded quickly. 

_ >>Incoming  
You don’t believe that any more than I do. _

Dean did not respond. A few minutes later, Jo sent one more text with an air of finality on the matter. 

_ >>Incoming  
If you want him back, you’re gonna have to do some serious groveling. _

Dropping the phone on the floor, and his face into his hands, Dean sighed heavily. He was in love with Castiel. Jo knew it, Bobby and Missouri knew it, Sam knew it, and he had a sinking feeling that Cas knew it too. That’s why this hurt so much. Cas knew he wasn't being treated fairly, and he left. Wanted to show Dean how much better he deserved. 

Dean was in trouble, as he was used to feeling when it came to Cas. But he didn’t know how to get out of it this time. 

**Notes for the Chapter:**

> And here we are at the end of the year. As a time for reflection, I'd like to take time for the moments that made this story possible, and for the life events that got in the way. Without spending too many words on it, I'd like to thank you for your continued support in reading and commenting. We are nearing the end of this story, though it's not quite at this moment. I hope to have more time to write in the coming days and weeks. 
> 
> I wish you and your family a wonderful holiday season, and a very happy New Year's. 
> 
> -azo


	17. Mr. Sandman

**Summary for the Chapter:**

> Life moves on for some.

_Winter, five months later_

Three rows of dancers stood, hands clasped behind backs and heads held high. The music started, sensuous and rhythmic. From off to the side, a voice, “And a-five, six, seven, eight-!” The girls spun neatly to the right for half a four-count and then dropped their hands to the floor, keeping their knees straight as they slowly straightened up, flicking their hair out of their faces. Some of the girls had ponytails tied high, while others let their long tresses flip freely with their motion. Anna, clad only in short-shorts and a sports bra with her heels, started her line on a series of slow squats, going a bit lower each time, flipping her red hair over her shoulder. The director called over the music, “Wonderful Anna! Keep it up everyone!” Castiel glanced up at the line of girls, coloring in a stripe of shadow in his sketch book as it hit the dark haired dancer in the back row. 

If he was being honest, Castiel had never given too much thought to Anna’s work, preferring those in the crowd than those on stage. Still, the well-lit studio in a dusty corner of a small Kansas town provided a sort of inspiration he didn’t get often anymore. Almost five months, and it seemed like he and Anna were both starting to settle down from the big city. 

Kansas was empty. Sure, it had the perks of KC—all the night life that Anna craved but Castiel hated—but out here, things were… quieter. Anna had been willing to start over again in this little town, so far away from what they knew, Chicago or otherwise, and for that Castiel would be eternally grateful. Their compromise though, was that they go somewhere Anna could dance—really dance. And yeah, she still twirled around at night for dollar bills sometimes, but her day job was now split between taking ballet classes and teaching five year olds to plié properly. Anna was so deliriously happy, Castiel couldn’t help but be glad for her. 

One of the girls tripped and stumbled into the dancer next to her, causing a chain reaction that wound up with the entirety of Anna’s line on the ground. Castiel leapt to his feet to help, but by the time the instructor stalked forward from the back of the room calling for “Cut!” the girls were already helping each other to their feet, giggling and playfully shoving each other. The director, a lean man with all his hair gelled back on the top and shaved sides, patted the clumsy girl on the back and stood at the front of the group. 

“Well, that was… better, ladies—“ the girls broke out in titters of laughter again, “—although I think I preferred it with less acrobatics. Take a five-minute break and come back to me.” He finished with a wide grin. His name was Trevor; he had a wonderful relationship with everyone in his little troupe of dancers from what Castiel could tell. 

Anna darted to the back to grab her water bottle, and came to slump next to where Castiel sat against the mirrored wall. Her skin was glistening with sweat and she dabbed at her temple with the back of her hand. “Sure you wanna draw us? We’re not the graceful dancers we thought we were.” Her smile was so bright—so much brighter than anything Castiel had ever seen from her in Chicago. It drew a grin from Castiel in kind. 

“Artistic license, I promise.” Anna rolled her eyes and shoved him. Castiel picked up his gum eraser and carved out the face of the dancer in the foreground. “And anyway, you were doing well before that mishap. Especially for a new routine.” 

Anna took a sip of water. “I know. I’m actually excited for this number. ’S better than that sleazy ‘40s crap Keith had us gyrating to. I might even send it to the professors!” One of the many concessions Anna had made for accompanying Castiel away from the city was that her dance program would allow her to continue earning credits if she took actual classes and submitted video evidence once every few weeks of her work. 

“I dunno, if you graduate, Trevor would be sad to lose you.” 

Shrugging, Anna said, “Truthfully, I dunno if I can bear to leave my kiddos after this.” She took another swig of her water and stood up to join the rest of the dancers, congregating again in the middle of the studio after their break. 

Castiel’s smile slipped off his face. In another lifetime, Anna would have made a wonderful mother. 

The rest of the rehearsal passed without further injury—although the dancer in question did get razzed a few more times during cool down—and before long, the sun outside the studio had set, leaving the world outside an opaque black. Trevor circled the girls up and gave notes and announcements. 

“—we’ll do costume try-on next week, so make sure to bring your nude tights… not pink… Salem…” he raised an eyebrow teasingly at a girl with long black hair, who rolled her eyes and clucked her tongue, “and then remember the primary classes need to have routines finalized before the end of the week, so please get me your songs!” 

Castiel smiled without looking up from his sketch pad. He’d sat in on Anna’s primary class a few times. A group of kindergartners trying to keep up with the Macarena would never be unfunny. Trevor dismissed the dancers and everyone stood up to leave. The girls went to pack up their kits, rolling up tights, slipping on street shoes, and shrugging into their parkas—winter in Kansas was not known for its balminess. Castiel reached for his bag as well, glancing around for his pencil case. Where was his smudger? 

He stood up, looking around. Running a hand through his hair—longer now than it had been in a while—he sighed. He’d just had it in his hand. And the nearest art supply store was at least an hour away in Lawrence. Damn. 

“Looking for this?” A smooth, tan hand offered the paper stick to him. Castiel looked up into the face of Trevor, still smiling gently. 

He took it and quickly zipped up his case. “Thanks… hate losing those.” He made the mistake of looking Trevor in the eye, warm green—bordering on hazel. The wrong shade of green, but close enough to be… problematic. 

Trevor smiled more fully, dimples cutting his cheeks. “Must’ve been working pretty hard, huh?” 

Chuckling, Castiel glanced down again. “There’s a lot of good energy in this room. Makes it easy to get inspired.” 

The dance instructor hesitated. “Can I see?” He seemed hopeful, but bashful. Castiel fumbled with his sketch pad, opening to the page he’d been working on. It was sketchy, but the outline of the studio and the lines of dancers were clear. Trevor whistled low, leaning in close to Castiel’s side. 

“That’s pretty badass. You even got the light from the window right.” Trevor grinned, looking up. “You really are an artist, aren’t you, Degas?” 

Castiel chuckled, and flipped a few pages back. A sketch of the bronze ballerina statue from the Joslyn Art Museum in Omaha stared back at them. “Something like that. I’ve always admired his work.” 

“So, you’re into dancers, huh? Explains why you and Anna are together.” Trevor sounded wistful to Castiel, but it might have just been his imagination. 

Stuttering, Castiel tripped out, “N-no, Anna and I… we’re just—“ 

Trevor rubbed the back of his neck and grimaced, “Sorry. That was—that was dumb to assume and—“ 

“—and I don’t even like women!” Castiel blurted and then blanched. He felt like his eyes must be the size of dinner plates in his mortification. 

Anna called his name across the studio. The two men looked up, Castiel felt his face blush hot immediately. Gesturing towards the lobby, Anna cocked her head in question. The studio was empty save for the three of them. Castiel cleared his throat and stepped away. He shouldered his bag and held up a finger, telling her he’d be there in a minute. Turning back to Trevor, he sighed. “That was inappropriate, my apologies.” He took his sketch pad from the other man and quickly stuffed it in his bag. He started towards the door, gesturing for Anna to hurry up and go out to the lobby, fully intent on following and never coming back. Fuck Castiel’s life and his loose lips around stupidly pretty green eyes. Anna blinked, but followed Castiel’s insane gestures, holding the door open for him. He couldn’t bear to glance backwards at the man who was certainly going to be weirded out the next time Castiel asked to observe his class.

As Castiel started up the car, Anna stowed her bag in the backseat. “So are you and Trevor gonna bang or not?” 

Castiel banged his head on the wheel. “I just told him I didn’t like women when he was asking about my art. I doubt he’ll even let me back in the building.” 

Clucking in sympathy, Anna patted his arm. “He’s pretty, isn’t he? It’s okay, I was a mess around him the first few weeks too. ‘Course, it was different for me, because he wasn’t even batting for my team.” 

“… what?”

“He’s gay, Castiel. He was hitting on you.” 

_“… what?”_

“I know, it’s hard to tell when the guy isn’t outright waving his dick in your face, but yeah.” Anna said, flatly, “Typically, normal people try to strike up normal conversation with the person they’re trying to hit on… in a really normal fashion.” 

Castiel swallowed. “I thought he looked at me like I was crazy.” 

Anna shrugged, “You are kinda crazy.” 

“Shut up.” Castiel started the car, backing out of the spot and heading towards their shared apartment a few blocks away. It was a huge step above their shoe box in Chicago, to put it lightly. Castiel had his own bedroom, he didn’t have to sleep on the couch and scrounge up whatever change he could get to pay his half of the rent. He worked commissions here and there, small businesses needing logos, blue-haired ladies angling for auction items for their churches, the local high school needing a new mural for their commons area. He wasn’t getting rich anytime soon, but it was enough to keep himself and Anna comfortable in small-town Kansas. 

As they turned down Elm, Anna broke the silence again. “But really… are you and Trevor gonna bang?” 

Castiel sighed. “Anna…” 

“You know, it’s not… bad to want to be with someone, Castiel. Like, again. You can have… something again.” Anna said quietly. 

Something. If he wanted something after Dean. Was he even capable of having something normal? His extracurricular career didn’t leave a lot of room for “regular” relationships. 

“You’d really let me sleep with your dance instructor?” 

Anna thumbed through her phone. “Might as well be one of us. We’ve earned some fun.” 

Castiel couldn’t get the thought out of his mind, like a fly buzzing around smacking into the sides of his brain. _“You can have something again.”_ Did he want something again? Something totally different than what he had, maybe. But not the same thing again. He couldn’t bear it. 

…

“You wanna just wait out in the car then?” Anna didn’t look up as she sorted through her bag, turning to grab her pointe shoes from the back seat. 

Castiel gripped the steering wheel harder, breathing out through his nose. “No, I can do it. I need to finish the piece.” 

Anna raised an eyebrow. “Are you gonna humiliate yourself again against someone else’s homosexuality?” 

“No!” Castiel paused. “Maybe!” 

Snorting, Anna popped the handle on the door and stepped out. “Well, come on then Casanova. You can sit quietly in the corner and romance my dance instructor from the sidelines.” 

Castiel scrambled out of the car to follow, hurrying to push the lock button on the keys. “I’m not—why did you call me that? … wait up!” 

The dancers didn’t suffer any unfortunate mishaps this time around, performing the entire routine flawlessly, and causing Castiel to applaud at the end. The girls grinned at each other and wiped at their brows as Trevor stepped forward, hands clasped in prayer. 

“Thank you ladies… that was phenomenal. Just amazing. I think we’re ready. This is great—we’ll get costumes on Tuesday, get to the stage on Thursday, and we’re golden.” He put his hands down. “Really. Great job everyone. I wanna run it again.” He hurried over to the tape player in the corner as the girls got back in their starting formations. The song started up again and Trevor circled around the room. 

Castiel smiled to himself and flipped to a new page. He started out with the far wall, sketching it in extremely lightly. He had sketched this room a thousand times, from a thousand angles, but this time he wanted something to be different. 

He wanted something different. 

He drew the girls in their starting positions, up straight. However, instead of their exercise gear, close cut to not get in their way, he drew them in long flowing robes, cascading over their shoulders, pooling at their feet. He drew so the satin of their robes hinted at the skin underneath, transparent enough to show the light, but opaque enough to drape in the right places. He drew them standing at attention, perhaps to a god they served; perhaps standing above a god who served them. He sketched out the edge of the room, blurred the details so it wasn’t as clearly a dance studio. Made it lighter, more ethereal, more like heaven. 

He drew them as angels. 

Castiel drew until the presence of someone next to him startled him out of his state. Trevor slid down the wall, keeping his eyes on his girls. “How’s the Sistine Chapel going, Da Vinci?” 

“Michaelangeo,” Castiel corrected automatically. He glanced up warily, “Sorry, that was impolite.” 

Trevor chuckled. “Hey, I’ll get it right on Jeopardy now. Thanks for the help.” He looked over and gave Castiel a warm smile. “Nice to see you again.” 

“Sorry to keep invading your space. You’re a really good instructor.” Castiel added on, having seen it for himself and from Anna. 

“Thanks. Never thought I’d find myself in a po-dunk town like this, though.” 

Castiel raised an eyebrow. “Where did you want to end up?” 

Shrugging, Trevor propped up his legs and rested his arms on his kneecaps. He typically wore loose sweats during rehearsal with a black tank on top with no shoes. “New York maybe? Omaha at least. Always wanted to see Chicago.” 

“It’s not all it’s cracked up to be.” Castiel snorts, turning back to his pad, “Smells something awful.” 

Trevor laughs. “Still better than a place that doesn’t even have a Target.” He calls for the girls to go again, for the last time he promises. 

Castiel hums good-naturedly and nervously shading in a shadow that probably imbalances the rest of the piece being so dark. He searches for something to say. He had the feeling that Trevor was trying to have a “normal conversation” with him, as Anna had said. 

“So you know Chicago? Used to live there or something?” Trevor asks, breaking the silence. 

“Or something is more like it. ’S not an easy place to live.” 

He shouldn’t hold a grudge against the entire city. It’s only crime was being the meeting place for Castiel and the man he thought he loved. No reason to discredit the entire place. Still, he wasn’t lying. Chicago would be a hard place to live, even without the bad memories. It didn’t have one of the highest crime rates for nothing. 

“Well, maybe you could tell me about it? Talk me out of it.” Trevor caught his attention with a smile. “Maybe over dinner?” 

Castiel swallowed, his grip tightening on his pencil. Anna was right. 

He’d hesitated just a touch too long. Trevor’s cheeks colored and he moved to push himself to his feet. “Sorry, apparently I can’t take a hint.” The song ended again, and he called the girls to a break, busying himself with the tape player. 

Thunking his head on the mirrored wall behind him, Castiel pushed himself to his feet. Anna sashayed over, bouncing her eyebrows the whole way. “Sooooo? How did that go? You two looked cozy.” 

“He asked me out to dinner.” 

Anna squealed, bouncing on her toes. “What did you say? This is a good thing right?” 

Castiel shrugged, feeling helpless. Truthfully, he didn’t know if it was a good thing or not. On one hand, this would be the perfect opportunity to move on with his life, to gain some semblance of normalcy. Make some real friends that weren’t after the same tips as he was, or forced to be his friend out of survival. Maybe even have a normal relationship. He wasn’t sure he knew what that would feel like. 

But on the other hand, did he want anything else? Time was supposed to heal wounds, but it’d been months and he still felt like he was drowning in how much he missed Dean. He missed working in the garage with him, making him smile, picking the discarded black olives off of his plate after pizza in the living room. And of course he missed whatever they had between them before he left, the chemistry and heat. He missed Missouri and Bobby and even his room that he barely spent any time in because he was so wrapped up in Dean’s world. He didn’t know if he was ready to let all of that go to start something new. The memories, painful as they were and tinged with the bitter taste of Dean asking him to leave, were better than pretending they didn’t happen. 

“I don’t—I don’t know what I should do.” He said, hearing his own voice shaking. 

Anna clutched his shoulder. He faintly noticed that she was sweaty again from all the energy she’d been exerting, but it wasn’t really on his radar. “Castiel. Don’t make this a demon, okay? It’s just dinner, not a proposal.” 

“I just… don’t know if I can be what he wants me to be for him.” He was aware he was making this overcomplicated, making this harder than it had to be, but he couldn’t stop himself. 

Cupping his face in her hands, Anna pulled him down to look him square in the eye. “You don’t have to be anything you don’t want to be. You can make the choice here.” 

Castiel took a breath and tried to steady himself. As the dancers came back from break and circled up for cool down stretches, he excused himself to the hall. He took a long drink from the fountain and paced up and down the short waiting area. 

He didn’t want this to be as big of a choice as it was seeming. He shouldn’t have to gear himself up for battle every time he had a conversation with a potential partner, or even a potential friend. He hated that his feelings getting hurt were the basis for everything else that would happen to him. 

Rehearsal must have ended, because the girls started coming through the door in twos and threes, parkas zipped and earmuffs on. Castiel huffed a sigh and steeled himself. He walked straight past Anna, who tried to catch his arm, past the rest of the dancers, to the far wall where the tape player and its operator stood. Trevor had his back to him, but the sound of someone clearing their throat made him turn around. 

“Would you like to accompany me to dinner tonight?” Castiel clenched his fist at his side, half terrified Trevor would say no, and equally terrified he would say yes. 

Trevor’s face split into a wide grin. “I’d be delighted to, Castiel. Pick you up at six?” 

It was a date.

…  
When Anna and Castiel first blew into town, things were pretty grim. They were fresh out of Omaha, where Jo’s mother had contacts. They spent time doing all the tourist-y stuff they could find—“Think of it like a vacation, Castiel!”—but soon they ran out things to do… and money. Castiel offered to split the money in the glove compartment with Anna, but even Dean Winchester’s forethought couldn’t keep up with two runaways with nothing to lose and miles to gain for too long. They had trekked their way south into Kansas, just looking for a place to set up a more permanent residence. Castiel was looking at different university’s art programs, while Anna wanted somewhere with good opportunities for dance. 

They found a small town where no one knew anyone from their past and a dance studio, and settled on the spot. 

The town was nice enough, clean streets and plenty of trees. It even had a library with a well-stocked mystery section. They hunkered down in a small motel for a few weeks, working odd jobs here and there, before they could put down a security deposit on a two-bedroom in the nicer part of the business district. 

Almost like real people. 

Trevor was exactly on time, arriving in a dark red Toyota. Castiel tried not to be relieved it was neither black or a Chevy. He greeted Castiel with a wide smile and opened his door for him like a true gentleman. He kept the radio turned down to a reasonable background level and made idle conversation with Castiel. 

“Unless you’re feeling a trip to Lawrence in the middle of the evening, I say we pick between pizza or semi-decent Mexican food.” 

Castiel chuckled. “Pizza sounds good.” 

The pizza restaurant was a small mom-n’-pop joint, with all the charms a town with no chain stores anywhere could bring. A friendly woman—probably one of the owners—seated them with a smile and a playful cuffing of Trevor’s ear as they sat down. Before long, they had a large steaming pepperoni pizza between the two of them.

“How long have you lived here?” Castiel asked. That was a perfectly normal question to ask on a date, right? 

Trevor licked sauce off his thumb. “I’m actually from further down south, almost by the Oklahoma border. Even smaller town than this.” 

Castiel nodded. “I’m from Pontiac, Illinois.” 

“Did you always know you wanted to be an artist?” 

“I went to school for it for a while. Almost graduated too, but… life got in the way, I guess.” Castiel said, looking down at his napkin. 

Trevor shrugged. “Tends to happen a lot, doesn’t it? I was going to be a marine biologist.” 

“There a lot of marine life in southern Kansas?” Trevor rolled his eyes and shoved him playfully. Castiel grinned more at the fact that he could still tease people and feel normal about it. 

Castiel tried to feel bad about how much he talked during dinner, but Trevor kept asking questions and being genuinely interested in his answers. He laughed when Castiel recounted his first life drawing class in which the model passed out from nerves… on Castiel’s easel. He asked to see pictures of his work and displayed a flattering amount of interest in his process. He even smiled kindly when Castiel described Sr. Guerrero and his cat Anita at Turning Pages. He very tactfully avoided any mention of Dean or his old job. 

In turn, Castiel learned that Trevor had loved the water so much as a child that he spent every summer in the pool and even did a turn as captain of the swim team at his high school. That he had a little sister named Salem with white blonde hair that was turning seven next month. That his first boyfriend dumped him in a corn field after prom their junior year… before asking for his best friend’s number. He learned that he attended his first dance class his first summer at camp, only because swimming club was full. That he still swam, but mostly as a way to exercise that was easier on the knee he busted his second year of college. 

It had been a long time since Castiel had spent so long with another person—besides Anna—that hadn’t tried to sleep with him for money. He found that he was genuinely enjoying his time with Trevor. So much so that when the owner—Mrs. Sterling, as Trevor called her—shooed them out the door with a box of leftovers, Castiel invited him to the apartment. Of course, not without a perfunctory text to Anna to get lost for a few hours. She owed him that; Castiel had been kicked out of the apartment more than once with one of Anna’s escapades.

Trevor agreed and took his hand on the way back to the car. 

…

“Nice place you got,” Trevor said, slinging his jacket over one of the mismatched dining room chairs Castiel and Anna had hijacked from the dump and refinished so they looked good as new. 

Castiel brought them both a beer from the fridge. “Thanks. Anna decorated most of it,” he admitted. 

Trevor accepted the beer and shot Castiel a wink. “Should put some of your work up. You’re great.” 

Working his jaw, Castiel watched as Trevor sipped his beer and examined the books collected in the small bookcase. He had a few options here. Trevor clearly liked him, liked him enough to spend time with him and keep spending time with him enough to come home with him. Trevor was certainly attractive—well-built, athletic, perfectly symmetrical face. His eyes were hazel in the dim light of his apartment. 

Decision made. 

He set his beer down on the counter and crossed to where Trevor stood. Castiel touched his shoulder softly and took his beer when he turned around. A confused smile was on Trevor’s face, but Castiel leaned in quickly to press his mouth against that smile instead. 

Trevor responded immediately, hands coming to Castiel’s waist. He didn’t press too quickly—ever the respectful gentleman—but made a grunt of approval when Castiel pulled him closer. He opened his mouth under Castiel’s ministrations, tasting faintly of the beer he’d been drinking. After a moment, they broke apart. 

“Sorry—I…” Castiel started. Trevor shook his head.

“Don’t apologize for that.” He dove back in and pulled Castiel to the couch. 

They landed hard, Castiel bouncing for a second before being gently tugged closer to Trevor’s side. 

It wasn’t anything like kissing Dean. There wasn’t the flurry of butterflies in his stomach, nor the rush of liquid heat to every extremity he had. Instead, it was a slow feeling of ease slipping through his veins. This was easy and good. Comforting. Castiel was more than relieved to find that he liked this. This was… normal. It was fun. It was making out on the couch after a good date. Trevor’s hands slid down to his waist and pulled suddenly, tugging Castiel into his lap. 

Suddenly, his hands clamped down on Castiel’s ass and hauled him closer, brushing their groins together. The feel of Trevor’s erection made Castiel freeze and then recoil like he’d been burned. “I-I’m sorry… Trevor—I’m sorry, I just… can’t.” 

Trevor backed off immediately and put some space between the two of them. “Hey, it’s okay. Listen, we don’t have to do anything, alright? We can just… kiss or—or whatever.” Trevor reached forward and gently held his face between his hands, pleading with his eyes. 

Castiel took a breath through his nose, trying to calm down. He grappled with the fabric on the sofa, clenching and unclenching his fingers. He closed his eyes and hated himself for the tear that slipped down his cheek. 

“Maybe I better just go.” Trevor pulled gently away from where they were seated on the couch. 

Castiel worked his mouth for a second. “I-I don’t want you to think that I… that I don’t—“ 

“As long as it wasn’t something I did.” Trevor said, scrubbing a hand through his hair. “I know it’s hard being… out in a town as small as this. I don’t want to make things hard on you, you just got here and all.” He smiled kindly. Castiel’s heart clenched with how badly he wanted to like Trevor. He’d had so few genuinely nice guys interested in his time. 

“It’s not.” Castiel’s throat hurt with the sadness, “There’s just… there’s someone else, and I didn’t want it to be an issue, because it’s been… months since I’ve heard from him, but…” 

Trevor smiled sadly down at the carpet. He stood up, and grabbed his coat off the back of the chair by the kitchen. “I get it. I woulda killed the guy that tried to pressure me into something I wasn’t ready for. ‘Specially when it comes to sex.” 

Castiel chuckled humorlessly. The amount of times he was pushed into something he wasn’t quite ready for was far too high for his liking. “For what it’s worth, I really wanted it to work with you and me. You’re… you’re great.” 

Placing a hand on Castiel’s shoulder, Trevor waited until he had Castiel’s attention. “Me too. But… wrong place, wrong time?” Castiel nodded. 

“I just need some time. Can we try again later? Maybe in a few weeks?” 

The hand on his shoulder turned into a gentle, good-natured nudge. “Don’t worry about it. We can take it slow. You tell me to stop, and I’ll stop.” 

Ice coursed through Castiel’s veins at Trevor’s words. He remembered Dean saying the same phrase exactly to him in the middle of his overly-clean living room, right before they started this mess. 

“Come on, walk me down at least?” 

Castiel shook himself, pushing himself to his feet to grab his own coat. He left the door propped open just a crack as they left, so he didn’t have to take his keys. Dimly, he wondered when Anna would be back and if he should text her, letting her know that her absence, while appreciated, was no longer necessary. Then again, he could just use the alone time to think. 

He followed Trevor down the stairs, silence hanging above them almost oppressively. They stood outside the front door for a moment under the florescent light in the main arch. Trevor hesitated, chewing on his lip for a second. 

“Are you still going to come to the dance studio tomorrow? Dress rehearsal should be a good time for some drawings.” Trevor tried to smile, but the stress in his eyes betrayed his worry that he might never see Castiel again. 

Castiel kicked a loose stone off the concrete slab and into the bushes. “Yeah, I’ll be there.” 

Trevor visibly relaxed. “Cool. I’ll see you then.” He turned to go, but paused, turning back, conflict clear on his face. “Can I kiss you goodnight?” 

“Yes.” 

Castiel pressed all of himself against Trevor as they met. He wanted so badly to be able to be okay, to be normal, after Chicago. He apologized with the way his tongue danced with Trevor’s, pulling a soft grunt of appreciation out of him. When they parted, Trevor licked his lips and smiled. 

“Well, whoever it is that has your heart… he’s a lucky bastard.” Trevor gave him one last peck on the cheek and started back towards his car, glancing over his shoulder a few times. 

Castiel watched the dark red car drive away, headlights flashing over the other cars in the parking lot. It passed over a sleek black car with Illinois plates that made Castiel blink. 

He furrowed his brow. It couldn’t be. That’d be crazy. Five months later, and he’s still seeing things where he doesn’t want to be. He turned back to go into the building, but stopped directly inside the lobby. He sighed and cursed himself, turning around again and shouldering the door open. He reached into the bushes where he found the loose stone and knelt to tuck it into the hinge of the metal joint, stopping the door from closing all the way. He wasn’t paranoid… he just had to check. 

Shoving his hands in his pockets against the chill, he wandered slowly towards the black car, growing more certain with each step that he’d seen this car before. That he was intimately acquainted with this car. The engine wasn’t running, but Castiel could see someone sitting in the front seat. He pulled out his phone, shining the flashlight app at full brightness. The person sitting in the front seat put up a hand against the sudden light as Castiel came to stand right by the driver’s side window. Slowly, the window creaked as it was rolled down. A man sat in the seat, shoulders covered with a leather jacket, flannel evident underneath. He moved the beam upwards, towards the stranger’s face, lighting across a set of perfect cheekbones and a plush mouth, and upwards…

Castiel stopped cold, almost dropping his phone, but catching it in time. “No…” 

A slow smile spread across the man’s handsome face, loss and pain still visible in his apple-green eyes, even as they lit up in recognition. “Heya Cas.”

**Notes for the Chapter:**

> ... hey. I know most of you may have moved on after a five-month hiatus. For the two of you still reading... surprise! 
> 
> Sorry.  
> -azo


	18. The Suburbs

**Summary for the Chapter:**

> A big, heaping helping of pining and flipped perspective.

Dean spends a lot of time alone these days. 

Missouri has stopped trying to lure him upstairs for what she calls a “proper family dinner” because she knows it’s no use, and he just won’t go. He works in the garage, goes to work (what’s left of it), runs around the neighborhood when he can’t stand the feeling of his own house, goes to bed. He doesn’t go to bars, he doesn’t call Sam as often as he should, and he doesn’t go near the covered canvas in the corner of his workspace. 

He thinks about things. He thinks about blue eyes; cast downwards in sorrow, flaring in anger, empty with pain. He thinks about colors, splashed on a canvas and hung on his wall in a tribute to his inability to communicate how he feels to another person who is equally bad at knowing what he’s feeling. He also thinks about the particular shade of blue that’s missing from his garage. He thinks about how he can’t seem to get the timeline for giving gifts right. He thinks about how giving a car to someone else didn’t quite go how he pictured, and now he doesn’t even have the delight of seeing it parked next to his own Impala, like it belonged there. He thinks about the envelope in the glove compartment of a blue car that he goes half-crazy wondering if it’s been opened yet or not, thrown away in a fit of rage, or kept in a nightstand somewhere in hope. He thinks about how stupid it was to leave it just in the glovebox, instead of in his desk or somewhere he wouldn’t have to regret not taking it. He thinks about how he should have found a better way to tell someone how he feels than by a stupid piece of paper folded into a lame security envelope. 

He drinks a lot when he thinks about that envelope.

When he does make it out of the cavernous place he calls home, he drives. Even though the traffic is as terrible as it ever is, he drives through the streets, barely knowing where he is. He keeps just enough of his head to avoid hitting anything or anyone, but he just goes. Sometimes he’ll walk around parts of the city he never got the chance to see. He spends a lot of time at the Pier now, smiling politely at the families crowded around a camera, and generally avoiding all puddles of melted ice cream along the way. He likes the view of the water, of the boats, of the view of his own house from afar. It’s nice seeing the place like everyone else sees it; an enigma across the lake, shrouded by trees and privacy. He always keeps watch for someone familiar with dark hair and a wry smile, but he never sees anyone worth noticing. He wonders if there’s anyone like that in the city anymore, or if they’ve cleared out by now. 

Somewhere inside, Dean knows he’s not handling things correctly. He should be able to be an adult and move on, maybe go meet someone new and have fun. It’s been months. Months without even knowing if Castiel—he can’t call him Cas anymore—even cares enough to remember him. And yeah, Dean knows he has no place getting upset, he was the one who told Castiel to leave, offered him a car. He wanted Castiel to yell, to get angry. Angrier than he did anyway. Dean was dumb enough to think that what they had was worth fighting for. He was so sure in the car before the phone call. So sure that he was ready to give all of himself for the first time. Not even in a sexual way, although Dean had been stressing about taking that step for a while, because he had been with other people. It hadn’t ever felt so… real before. 

But every time Dean starts down that path, he has to mentally shake himself. If he gets too caught up in the what-ifs, he ends up looking down the neck of a bottle of Jack, and he’d like to wake up without a headache at least once this week. He knows Missouri and Bobby are worried. He knows Sam is stressed about trying to get him out of the house and into some sense of normalcy again. He knows he at least needs to push himself into moving on, even if it doesn’t feel genuine right now, at least for his family’s sake. He’s sick and tired of feeling so broken up about this, the guilt is crushing him. What hurts him more is that he doesn’t have any idea where Castiel could be. Jo offered to find out more than once, but he turned her down each time. Castiel deserved more than Dean stalking him out of a broken heart. He didn’t deserve to be in Castiel’s presence right now. So he spends time alone and he thinks and he handles things. 

…

Sam calls at least once a week, sometimes leaving a message, sometimes not. Each time, he asks Dean to call him back, just to see how he’s doing. He doesn’t know much of the specifics, but he knows his older brother is hurting and it has everything to do with the frankly ridiculous news story that held the media’s attention for a few days before the local government caused another uproar. Sam is lucky enough to drag Dean out to dinner once or twice a month. They mostly go the Roadhouse, letting Ellen fuss over them for a while. Dean still doesn’t say much. Not to anyone. Sam tries not to take it personally. 

Once, Sam consulted Jo about it, probably the only person outside of Ellen who knew the both of them inside and out. “It’s like Benny, but worse. He’s never carried on this long,” he murmured into the phone, twisting the end of his tie around his finger. “I wish I knew what made this time so different.” 

Jo sighed on the other side. “I mean, I know I only met the guy once, but Castiel seemed as broken up about it as Dean does. It was like their whole world had fallen apart.” 

“Do you think it’s love?” He asks, only half-kidding.

“If it was, I’m not sure what it is now.” 

Sam frowned. “What do you mean?” 

“Anna texts every once in a while,” Jo said. “She and Castiel seemed to be doing alright. They’re settled down in some little town in Kansas. I have the address.” 

Well that was certainly curious. “Why Kansas?” 

“No idea. I don’t wanna pry too close into someone else’s business. ‘Specially since it’s a friend-of-a-friend situation, ya know?” Sam can practically hear her shrugging. 

“I get it. I just wish Dean would… talk about it or something. Even just to bitch about it. This is just… pining.” 

“Face it, Sam. Dean’s not gonna crack unless he wants to. Man’s a human bottle of unexpressed emotion.” 

Sam bid Jo farewell when she said she had to get back to the stage, leaving him to his thoughts. There was an uncomfortable amount of truth to what Jo said. Dean was very unlikely to tell anyone outright what was bothering him. He had a laundry list of distractions; his cars, his company, (until very recently) anything that moved. Dean Winchester was not a man to be tied down for long. When something stopped working for him, he moved on. No questions asked, no hard feelings. A business transaction. This puttering around the garage, avoiding dinner invitations even from Sarah, and general moping, however… 

If Sam didn’t know any better, he’d have thought his big brother actually was in love. 

The door to the condo opened. Sarah smacked a kiss on his temple when she breezed in the door, carrying a plastic bag of bananas and packaged spinach. “How’s the best lawyer in all of Chicago?” 

“Frustrated.” He answered absent-mindedly. Their condo had a very open floor plan, which Sam appreciated. He could see and have a conversation with Sarah, regardless if he was in the kitchen, dining room, living room, or foyer. 

She stopped in the kitchen. “Is that so? Are we talking frustrated or _frustrated_?” She bounced her eyebrows suggestively. 

Grinning, Sam stood and moved across the floor to wrap his arms around her from behind. “I love you, but I don’t think I want to see that bedroom anymore than we have been.” It had been a long and hard (heh) road trying to conceive. Of course, it hadn’t been for lack of trying, and the doctor’s advice was to just be patient and let nature take its course. Sarah and Sam were both healthy adults with completely normal levels of hormones. To Sam, it felt like they’d been trying for ages. 

“Maybe we need to switch up our locales.” She ground back into him and wriggled her hips a bit. Sam grunted appreciatively. 

“Not that I’m not totally down for sex on the kitchen table, but I was gonna go over and see Dean.” 

Sarah turned around, sympathy clear in her eyes. “He’s still not himself?” 

Sam shook his head. “Thought I’d try to get him over here actually. That okay?” 

“We’ve got too much pasta around here anyway for just us.” 

“I’ll tell him that.” 

“Still,” Sarah pulls away and goes to the pantry, one of the only doors in the condo, and opens it, taking stock of ingredients for what Sam hopes is chicken parmesan, “I can’t say I really blame the guy. That Castiel guy seemed to really have a big chunk of his heart. Can’t be easy to just get over that.” 

Leaning against the counter, Sam crosses his arms. “D’you think he’s being… I dunno, weird about it though?”

“Weird how?”

“Well, usually he’d be… over it by now I guess. It’s just… different. I don’t even know how to help him.” 

Sarah grabbed a jar and set it on the counter, pushing it back for later. She turned to pull a Brita pitcher out of the fridge, setting it next to two glasses. She poured water into both and offered one to Sam. “Think of it this way, how are you gonna react if your very happily married brother tries to offer relationship advice when you’re still picking up the pieces of your pulverized heart.” 

“You think he’s in love.” 

“I think,” Sarah took a sip of her water, “that Dean didn’t know how deep he was in until it started affecting other people.” 

Sam considered this. Dean didn’t take a lot for himself. His business was founded on the very idea of giving to others what he could, helping them along. He had his fancy house, sure. But he didn’t buy anything until he was sure he could provide for his company and every employee he hired. His people were among some of the highest compensated legal assistants in the city, fully insured with benefits and everything. Dean had never taken anything selfishly. Didn’t take what he believed wasn’t his. And suddenly, someone else was out of a job, out of a future, because of him. And it wasn’t just anyone, but someone Dean put a lot of emotional energy into. 

Sam raised his eyebrows. Huh. Dean was in love. 

…

“Spaghetti. Mountains of it. As far as you can see, and more than even you can eat.” Sam said in lieu of a greeting to a seemingly empty garage, trying his best to sound enticing. Missouri had pulled him aside as soon as he had walked in the door of the ostentatious mansion and voiced her concerns that she hadn’t seen Dean eat in almost three weeks. Sam had nodded pityingly, assuring her that he would do some damndest to get some nutrition in Dean that wasn’t coffee or alcohol. Which brought him down here to what Dean called a ‘garage’ and what everyone else referred to as a ‘Iron Man Cave.’

It took more than a few seconds, but there was movement over on the far side of the garage. Far away from the sheet Dean refused to let anyone near, he noticed. Sam rolled his eyes indulgently as Dean poked his head out from underneath a heap of scrap metal that probably was more useful in a dump. This is what it took. 

“Is there gonna be meatballs?” 

Really, this was already going better than the last dinner invitation he had extended Dean, which was ignored pointedly until he gave up and left the room. He’d received a text later with only one word, _Sorry_. And that was the end of that. So yeah, big improvement. 

“Do we ever make pasta without meatballs?”

Dean sat up suddenly and pointed the wrench at Sam. “Yes, sometimes you make those weird-ass tofu meatballs. They don’t even deserve the privilege of being called meatballs.” 

“Okay, I promise. All red meat. No tofu.” And that wasn’t _totally_ a lie. He just had to text Sarah real quick and tell her to defrost the hamburger in the freezer before Dean came over and found out his original meal was supposed to include more soy than he was ready for. 

Sam was patient as Dean stood up and dusted off his ratty jeans. He did look thinner as Missouri had feared, Sam noticed. He looked tired too, like he hadn’t slept properly in about a month. Maybe more. Sam convinced him to put on something a little less oil stained and herded him into the black Challenger that Dean never missed an opportunity to tease him about. _“It’s too plastic to be a real car, dude.”_ He was pleased this aspect of Dean’s personality hadn’t changed at least. He dutifully endured his big brother teasing him the whole way to the condo. 

When they arrived, Sarah was waiting by the door to envelope Dean in a warm hug the second they stepped through the door. Dean had always held a soft spot for his brother’s wife, and he all but melted into her embrace, wrapping his arms tight around her and ducking into her shoulder. 

“It’s good to see you, Dean. We missed you around here.” 

Dean didn’t respond, but held her tight for a few seconds longer before stepping away, mysteriously swiping at his eyes and loudly going on a search for the beer. Sam was suddenly overcome by how weakly Dean had been holding himself together. He shared a worried glance with Sarah before following Dean into the kitchen/dining area. 

…

To Sam’s credit, they made it all the way through salad and one round of spaghetti before he tried pointing out the painfully obvious truth to Dean. 

“D’you think you should talk to someone about how you’re coping with this?” 

And to Dean’s credit, he only spent two seconds frozen with his food falling out of his mouth. “What makes you think I’m not coping correctly? And that’s assuming there’s anything to cope with.” He asked, carefully blank. 

“I know you’re upset about Cas.” 

Sam watched Dean clench around his fork so hard his knuckles turned white. He felt bad about being so blunt, but his brother was hurting and he had to do what he could. 

Dean was quiet when he responded. “There’s no one I can talk to about that.” He twirled his fork around his plate, not picking up any pasta and not seeming to notice.

“I know breaking up sucks, it feels like the worst thing in the world, but—“ 

“Sam, no.” Dean wasn’t particularly loud, but the tone of his voice stopped Sam in his tracks. That was his voice that booked no argument, no further discussion. 

The silence was mercifully broken by Sarah. “I think what Sam is trying to say is that we’ve noticed you haven’t been yourself lately, and we were hoping to help in some way.” God bless his wife. She always knew what to say, especially when Sam tripped over his own helpfulness. 

A muscle in Dean’s jaw tensed, but he at least answered her with less animosity. “I know I fucked up, alright? There isn’t much I can do at this point.” He set his fork down. “I don’t want to force myself on someone who doesn’t even want me around, and I definitely don’t wanna go get my head shrunk about it.” 

Sarah shrugged at Sam. Sam took a deep breath. Dean might actually deck him for this in his own home, in front of his wife. 

“Dean you’re in love.”

“It doesn’t make a difference,” Dean responded listlessly, “I messed up, I have to live with that.”

Well that was definitely a surprise. Sam was fully prepared to have to explain it to Dean, with flip charts and everything detailing how painfully obvious it was to everyone that knew them they were both in deep. The fact that Dean already knew and accepted this fact put the issue in a new perspective. 

Sam fell silent again. He’d have to rework through this issue. Dean in love was not a happy man. If anything, being self-aware of how he felt was paralyzing Dean in a way Sam was not used to seeing. 

Miraculously, Sam was not left in agonizing and awkward silence for long. “He was dyin’ to get away from me. Couldn’t have drove outta here faster if he tried.” Dean cut in with the most heartbroken tone Sam had ever heard out of his brother. 

Sarah broke in, “What did you say to him?” 

Dean scoffed. “What difference does that make?”

“Was he absolutely sure you wanted him to leave?” She asked, gently. “Did you tell him to leave?”  
“Yeah, I basically told him as much.” 

“Did you tell him why?” 

That threw Dean for a loop. “I—yeah.” No one had asked him that before, clearly. 

“What did you tell him?” Sarah had found an edge and she was prying. Sam wanted to caution her to be careful, to shield her when Dean would eventually lash out in frustration. Dean wouldn’t handle this for much longer.

“I told him—“ Dean’s eyes slowly grew to the size of dinner plates. Sam could practically see him replaying whatever breakup moment he and Cas had in his brain. “I said… oh god.” He dropped the fork and sank his head into his hands. 

Holy shit. Was this the breakthrough? 

Sam reached out to grasp his shoulder, grounding him. “Dean.” 

“Oh no, Sammy—I…” 

“What did you say?” 

“I said things would be easier if we just broke it off.”

Sam glanced over at Sarah. This was at least a start to talking through the issue like an adult. “Did you say anything else?” He pitched his voice to be soothing, like he was calming a victim of an accident or a screaming toddler. 

When Dean looked up, he was stricken, a haunted expression laying heavy in his eyes. “No. Sammy, he thinks I kicked him out because of the news story.” 

Sam’s heart broke for Dean, not for the first time. The media had really done a number on Dean and had a lot to answer for. “Okay, we just gotta—“ 

“How could I do that to him?” Dean was getting a hysterical tone. 

“You mean you’ve spent this whole time not knowing why he was mad?” Sam had to ask, incredulously. Sarah gave him a swift kick under the table, having gotten up to stand on Dean’s other side and rubbing his shoulder reassuringly. 

“I thought he was just getting away from all the attention. I mean, the media circus, the scholarship. I… I caused a heap of trouble for him. Even before all this.” 

Sam spoke slowly, feeling the weight of his words the whole time. “And you don’t think sending him away was the cherry on top of his bad day?” It wasn’t meant to be an accusation, and he prayed Dean wouldn’t take it as one. 

Dean stared at a spot on the table. “Sammy, I really fucked up.” 

“We can fix this, Dean. We can.” 

Dean turned his frantic gaze on his little brother. “How? I don’t see a way out of this.” 

Sam gripped his shoulder. “Do you want to make this right? Do you want him back?” 

“I want to make this right, but I don’t know if he’d come back even if he knew.” Dean’s voice shrank into itself, sounding flayed and miserable. 

Shrugging, Sam pulled back. “Only way to know is to ask. Fall on your knees and beg forgiveness and all that.” 

Suddenly, Dean stood, nearly knocking over his chair. “I gotta find him.” 

“Then we’ll get you set up. And you’ll find him.” 

“Do you know where he is?” Dean looked half-crazed now. Sarah stepped back and shook her head. She gathered empty dishes and took them to the sink, muttering under her breath about _‘overdramatic Winchesters.’_

“No… but I know someone who might.” Sam raced to get his cell from the arm of the sofa. He pulled up his list of contacts and scrolled to the J’s. He hoped whatever higher power had the reigns was feeling merciful. For all of them. 

…

This was by far the _dumbest_ thing Dean had ever found himself doing. Cruising through a little town just an hour south of Lawrence, his own hometown ages ago—barely even a home anymore—looking for a familiar blue roadster. He should be arrested. He should be thrown in prison and he’d go. Arrested for disturbing the peace. Because that’s the only way he can see this going down, if he even finds Cas. This is either going to end in crushing disappointment or angry tears, and Dean really isn’t looking forward to either. Still, he can’t sleep knowing Cas doesn’t know how much he means to Dean, and that he only sent Cas away for fear Dean was keeping him from his dreams. 

The drive from Chicago had been long. He always hated driving more than four hours anywhere anymore, but he hated flying worse. His back ached something fierce and he was more than ready to catch a nap. He hadn’t seen a motel in miles, so he figured if this… rescue plan whatever it was didn’t work out, he could conk out in his car somewhere quiet. For now though, he drove. 

He knew the area in a vague sense. He was sure he had cruised through here at least once with his parents in an effort to explore the old place on a visit. Dean thought he might still have an elderly aunt that lived nearby. On the main road, he took in the charming view presented by the neat one-story shops with brightly colored awnings over wide sidewalks. Parking was available on both sides of the street, and not a parking meter to be found. The municipal trash cans were even well-kept. In the cold of the winter night, he didn’t see anyone walking around aimlessly after dark—probably too small of a town to even do that here. That was one thing he appreciated about downtown Chicago, the streets were always alive, even if the rest of the city was fast asleep. He passed a school, a crumbling cemetery, and a building with a brightly colored mural on the side, visible even in the yellow street light. 

He slowed down to get a better look. The mural looked familiar but he couldn’t place how he recognized it. Was it a copy of a piece of art he’d seen? Something in the brushstrokes looked… like he’d seen it before. He shook his head and kept going, keeping a wary glance out for the royal blue roadster he’d spent months tinkering with. He hoped against hope that no county sheriffs were out patrolling, because he’d have a hard time explaining why he was driving at Sunday speeds through the small town in the middle of the night. 

Basically, Dean reasoned, he just had to look for the car. He hoped to whoever was listening that Castiel hadn’t sold the damn thing out of spite. It would make his search a lot harder… and far creepier than he intended. It wasn’t like he was going to call up the local fuzz and say Cas had stolen it. He wasn’t even going to try to get it back. It was a gift when it was given—no matter how it was received—and it was staying a gift. Dean wasn’t sure what he would do with it back in his garage again anyway. He just wanted to see. He wasn’t even really optimistic on talking now that he was here. He just needed to know Cas was okay. 

At his side, Dean’s cell blared out the ringtone for Missoui calling—Jimi Hendrix _The Wind Cries Mary_ —with the same demanding tone that its owner had. He spared it a glance, but let it ring through to voicemail. He rolled his eyes when his phone lit up again to let him know Missouri had also taken the liberty of sending him several text messages, just to make sure he knew she wanted his attention.

_Received:  
You trying to give me a heart attack boy? Just up and leave without telling nobody where you’re going?_

_Received:  
I thought about calling Sam but you’re a grown man_

_Received:  
I hope you aren’t doing anything dumb_

Dean rolled his eyes, grabbing up his phone with the full intention to shoot a snarking text back, while definitely keeping his eyes on the road at all times. His thumb paused over the keyboard however, and what he typed ended up less snarky than he wanted. 

_Sent:  
I’m in Kansas. Gotta find Cas._

Missouri’s reply came less than five seconds later, telling Dean he had absolutely worried the shit out of her when he took off in a huff of squealing tires and manpain. 

_Received:  
Good luck sugar. Tell him I said hello.  <3 _

He squinted at the last character for several seconds before realizing it was a heart. He sighed. When did he get so old? 

The north part of town proved to be a bust; all two of the apartment complexes had been populated with second-hand Toyotas and a beat up Honda. He took the main road again and kept his eyes peeled for the roadster. He supposed there was a good chance Cas didn’t even have the car anymore, sold for money or just to get rid of it, but he felt it. That car was here, and it would lead him to Cas. 

He pulled into the parking lot behind a row of shops lining the main road, each with a second level. He turned off the car and sighed. Maybe this was pointless. Maybe this was the universe telling him to give it up already. _Take a hike, buddy_ , he could almost hear, _You ruined this already good and proper. Time to move on._

He rubbed at his eyes, tiredness settling in now that he had stopped. He glanced around. Nothing would be open this time of night in a town this small. He might as well sleep in the car. He glanced in the mirrors of the Impala. There wasn’t a whole lot around to be honest. The row of stores behind him looked locked up tight, except for the small lobbies that went up to the second-story apartments were it up. From the back, it looked like a pet store, a hardware store, and maybe a specialty… model supply store? Dean shook his head. Small towns. A flash of blue tucked into a side street caught his eye, almost like it was waiting for him to notice it. He sat up suddenly, nearly knocking himself in the head. That was the roadster, he was more than sure of it. He looked around wildly, as if Cas would be leaning on a tree somewhere, just waiting for him to get his head out of his ass. Cas had to live above one of these shops then! 

Suddenly, the back door to the hardware store opened and a tall guy stepped out, followed by—…Cas? 

No fuckin’ way he was this lucky. 

Dean bit his lip, this was a bad idea. He can’t have really expected to just show up out of the blue—after months of radio silence—and walk away with a smile on his face. Life didn’t work like that, and it certainly didn’t work that way for Dean Winchester. He watched the guy hang back with Cas on the small concrete porch and chat for a bit. When he leaned in to plant one on Castiel, Dean had to look away, telling himself the hot tears he could feel pushing at his eyeballs was just because the heater was on too high. His grip on the steering wheel was turning his knuckles white. This was a bad idea, this was a terrible idea. He never should have listened to Sam, he should have kept on with his coping method of drinking and ignoring until he either drank away the memories or became an old man cooped up in his lakeside mansion. Would have been a hell of a lot easier than this. Three seconds and he had gone from elation at finding Cas after all this time to a sucking feeling deep in his chest. 

The guy—tall with good hair, nicer than Dean’s—loped gracefully away to his car. Dean didn’t even have to be relatively close to see the warm smile plastered on the dude’s face. Not that he could blame the guy, he was sure he’d had a more than similar expression on his face the first time he’d laid one on Cas. The guy wore closer-fitting pants than Dean ever tried to get away with, bowlegs considered. He was muscular, the kind of muscular that dancers and gymnasts had in spades. Functional muscle. Great, that meant he was some kinda artsy guy like Cas. Perfect fit, probably. He kept his eyes trained on Cas, feeling more like a creep with every passing moment. He shouldn’t be here, shouldn’t be intruding on this moment, but he had to see. He had to see that Cas was well and truly happy here away from the city and away from Dean. Maybe this was why Dean had found him. Maybe the universe was giving him a good kick in the head to go back home and leave Castiel to his life. Dean clenched and unclenched his hands around the leather of the steering wheel. Maybe the universe wasn’t as benevolent as Dean wanted to believe. Dean’s eyes were glued with rapt attention as Cas watched the guy drive off, but he didn’t grin and wave, nor did he look down and blush, like one might expect after a good date with a potential partner. He just watched. 

Cas turned to go inside, casting a glance around the parking lot as he did. Dean froze as Cas’s gaze snagged on the tail end of the Impala, but relaxed as he went inside. Dean craned around to watch him in person, rather than from a mirror. Just to make sure he got upstairs, he reasoned. Definitely not to catch one last glimpse of him before making the long trek back to Chicago. Definitely not. 

Suddenly, Castiel spun around again and pushed the door open, propping it open. He stuck his hands in his pockets and walked out to the parking lot. Dean whipped around and panicked. He should have brought a different car, this was too recognizable for a stakeout operation. He didn’t dare move as Castiel rounded on his car, eyes moving across the license plate to the body of the car. This was it. Dean was done for. Cas was going to take a swing at the car out of spite or anger, and that was even before he got his hands on Dean. Dean didn’t think Cas would actually hit him or even really shout, but he wished he would. He wished he could get some tangible punishment for this overwhelming hole he put in himself. 

Cas was close now, edging up to the side of the car carefully. Dean considered ducking, just pretending he wasn’t in the car. That is was a weird coincidence that the car Castiel recognized just happened to _look_ like Dean’s Impala. He caught a glimpse of Castiel’s expression in the side mirror though, and immediately derailed that train of thought. 

Cas looked _pissed_.

He winced and rolled down the window, preparing himself to be yelled at or worse. Still, even as Cas stormed up to the car, Dean couldn’t help but take in his features like he was a man dying of thirst out in the desert. His hair had grown out a bit longer, curling on the sides and in the back. For once, he didn’t look so tired and drawn under his eyes. He looked well-rested and like he’d actually had a few decent meals in recent memory. Dean didn’t recognize the clothes he had on, a nice button up and dark jeans with a wool coat over top. When Dean had met Cas, it had been in the heat of summer. It was rare that Dean saw him in anything heavier than shirtsleeves. He looked taken care of. He looked good. He looked like any other twenty-one year old in America. Twenty-two now, Dean mentally corrected himself. Cas had his birthday in September. Another day he’d missed thanks to his stupidity. 

Dean was treated to watching Cas’s expression go from angry suspicion to shocked recognition as he registered who was sitting behind the wheel. “No-“ he heard, cut off as Cas’s words failed him. Dean grinned sheepishly at him. 

“Heya, Cas.”

**Notes for the Chapter:**

> Did I ever tell y'all how much I hate trying to put italics in a piece? Fuckin' worst. 
> 
> Thanks for reading! Just a question, but what do YOU think is in the envelope Dean's so worried about? 
> 
> Happy first day of June!   
> -azo


	19. Breathless

**Summary for the Chapter:**

> A visitor.

**Notes for the Chapter:**

> Hey, some casual trigger warnings for some negative self-talk if that's your thing.

Castiel couldn’t believe this. Just. Could _not_ believe this. 

“Dean.” He sounded flat and emotionless to his own ears. 

Inside the car, Dean was sputtering. “Cas… Castiel, listen—I know this is weird timing, and I’m probably the last person you wanna see right now—“

“Understatement!” Castiel scoffed, crossing his arms. “Why are you here?” 

Dean pursed his lips and stared at the wheel. The car wasn’t running, but it was clear he hadn’t been sitting here long. “I shouldn’t ask this, but will you go for a drive with me?” 

“Don’t want to be seen with me in public?” Castiel knew that was a low blow, especially after all this time and the detached persona he was going for. 

“I deserved that. Cas, I deserve so much worse than that.” His voice turned pleaded and he looked Castiel in the eye. “Can we please talk? If not in my car, then somewhere else?” 

“Now?” 

Dean froze. “No. Course not.” He pasted a smile on his face that Castiel could see through even in the dim light. “It’s late, and… yeah. I get it. You’re tired and-and… yeah, we can talk tomorrow or…? Some other time?”

Even after all the hurt this man had put him through, he couldn’t stand watching Dean fake being okay when they were both clearly not. He sighed. “How long did you drive?” 

“Ten hours.” Dean answered immediately, no sign of shame. “Took about another hour to find you.” 

Castiel backed up a step, keeping his eyes carefully away from Dean. He wondered if Ms. Williams was watching from her window the strange scene unfolding below. She’d probably corner him by the mailboxes tomorrow to ask for details about the strange man in the black car. “Come upstairs.” 

“Cas, really. It’s okay. I can find a motel or something if you wanna talk tomorrow—“

He turned his gaze purposely towards Dean, cranking up the pleading and adding in just a hint of batting his lashes. “Please come upstairs?” 

Dean undid his seat belt immediately.

Castiel led the way back into the building, kicking the rock aside that was holding the door open. He didn’t speak as Dean followed him, and neither did Dean. He let them both into his apartment, shutting the door firmly behind them. He turned back to the still-gorgeous man standing in a place he never thought he’d see him. “How on earth did you find me?” 

Dean grimaced as he took off his jacket and laid it carefully over a chair. The same chair Trevor had slung his coat over not an hour ago. “Is it too shitty of me to say I don’t want to tell you?” 

“I guess as long as you didn’t put every officer in the United States on APB to look for me.” Castiel was only half-joking. 

“I didn’t. Even I don’t have that kind of power.” 

“It’s not funny.”

“I’m not laughing.” 

Castiel ran his hand through his hair, messing it up further. He needed a distraction. The tension between them was building like it always had—fast and intensely. “You uh… want a beer? Or anything?” 

“No, no I’m fine.” Dean shifted from side to side like he wasn’t sure what he was doing here anymore than Castiel was. 

Castiel let himself collapse on the couch. “You can sit.” He indicated the other side to Dean, who gingerly took a seat as well, as if unsure of his welcome. 

“Why are you here, Dean.” Castiel said it, but not as a question. “I don’t think you just happened to be in town at eleven o’clock at night just as a coincidence.” He let every ounce of venom he felt bleed into his tone. 

Dean looked down at his hands. “No, it’s not. I’m… I’m here to apologize. I owe you that. As a minimum.” 

“Well, I’m sorry you drove all this way, but I’ve moved past it.” Dean looked up, his expression clearly wounded. Castiel was lying through his teeth, and he knew it, but he couldn’t let himself be weak to this man again. 

“Right, right. No, that makes sense.” Dean didn’t speak for several moments. He looked like he was measuring the weight of his next words. “You happy here?” 

“I am. I paint stuff for people around town. Anna teaches real dance classes.” 

Dean’s face lit up. “That’s your work on that building downtown. With the swirls and the—the… that blue you like. You got like a huge tube of it at that art store.” 

“Ultramarine.” Castiel barely managed to get out. He can’t believe Dean remembered that. 

“Yeah.” Dean got up and turned towards the bookcase, picking up titles and setting them down. “And you date.” He said without turning around. He doesn’t sound angry or upset. He’s just stating a fact. 

“Yes, that’s Trevor,” Cas said carefully. “He works at the dance studio and lets me sit in on rehearsals to draw sometimes. He’s very nice.” He can’t get a solid read on Dean’s response to this. He also didn’t know if he wanted Dean to be upset or indifferent more. 

“Good looking guy. Great hair.” 

Castiel hummed noncommittally. How Dean could find anything about anyone to feel insecure about himself was beyond him. 

“So you’re here then? Permanently?” Castiel recognized the subject change for what it was. 

“We’re staying for the time being. We wound up here after passing through Omaha. Seemed like a good spot to settle. For a while at least.” Castiel didn’t mention that he couldn’t stay in Omaha because there were too many people, and crowds reminded him too much of Chicago, and Chicago reminded him too much of Dean. 

“You know, I grew up about an hour from here.” Dean finally turned around, hands in his pockets. He looked like he was trying to make himself smaller in the space around him. 

“Thought you grew up in Boston.” 

“Did time there, sure. But… no place like home.” Dean finished with a tight smile. 

“Somehow I can’t imagine you amongst all the corn fields and Jayhawks gear.” 

“Hey, just because they’re not doin’ so hot anymore…” Dean’s actual smile dropped off his face. 

Castiel was struck by the moment in its surrealism. The clock Castiel hated and Anna loved ticked too loudly on the wall above the sink, which was dripping steadily. The lightbulb above them buzzed occasionally, and the couch had tatters on one corner where its previous owner had clearly had a cat. He was sitting in the middle of the most possessions he had ever owned in his entire life, and also in this space was the man that haunted Castiel’s dreams for months. He wished desperately he could read Dean’s mind, and get some idea of his angle here. What did he want, and why was it so important he was at Castiel’s door in the middle of the night? He found he had less idea of what to say to him than when they first met and Castiel was just trying to get rent money out of a potential john. He wanted to ask every single question in his head at once. 

“How is… everything?” He asked instead. 

“Um… it’s good. Missouri misses you something fierce. She says hi, actually. So… hi.” Dean actually waves his fingers in a miniature approximation of a greeting and Castiel can’t actually believe his life. 

“Be sure to tell her I said hi as well.” 

“Sure. Yeah, will do.” Dean looked down. 

Castiel wanted to keep him talking. He wanted to ask the most obvious question, ‘how badly did I screw up your life’ but instead he asked, “And how’s the company?” He didn’t know which answer would be hardest to hear, that nothing had changed and he threw away his whole life for no reason, or that everything Dean had worked for was in the ground because of him. 

“It’s fine. Charlie’s a genius at handling… everything. Press forgot about the whole thing in a week.” 

Castiel nodded, his mouth tight. “Great. Good to know it didn’t have any lasting effects. Wouldn’t want that kind of tarnish on a good name.” 

Dean looked stricken. “Cas—“ 

“No, I’m very happy it worked out for you, Dean.” He pushed up from the couch and walked over to the dining table where Castiel still had sketches spread out, scruffing them together in a pile. He didn’t think he’d make it to the dance studio tomorrow, like he’d told Trevor. He thought he’d spend the day under his covers instead. He’d lock the door so Anna wouldn’t bother him, of course. He just had to get Dean out of his apartment so he could get to his groveling. 

Dean was half off the sofa, reaching towards him. “Cas, I am so sorry. You’ll never know how sorr—“

Castiel cut him off. “Thank you, but it’s not necessary. Really, I’ve moved on from the experience.” 

Dean hesitated. He came around the table to face him with the wood of the table between them as a shield. “You’re happy?” 

“Very happy. Elated.” Castiel’s tone was clipped, and so very much a lie. “Now, if there’s anything else you need, Mr. Winchester—“

“Don’t you call me that. Not you.” Dean didn’t yell, but the broken way he pled with Castiel put him to enough of a full stop that he may as well have. 

“Dean—”

“Sorry.” Dean braced his hands on the chair in front of him, keeping his gaze firmly on the table. 

“What do you mean ‘not you’?” Castiel asked carefully. 

“I can’t… hear that. Not from you.” 

“People call you that all the time.” 

Dean hesitated. “It’s different coming from you.” 

“Why?” 

Grimacing, as if in pain, he finally looked up. “Dammit Cas, you know why. You’ve got to know.” 

Castiel felt himself getting angry. He was tired of pretending he meant something to Dean besides an easy lay. “No, I don’t. Why should I be any different? Just some whore you messed around with—“

“—God, Cas, stop saying that—”

“It’s true! You don’t like it, but that’s the truth. You paid me to use me, and now you wanna feel bad about it? Why?” Castiel stopped to take a breath. Dean stared at him with a curious look that was caught between overwhelming sadness and affection. “Tell me why.” He demanded again. 

When he spoke, Dean was quiet. “How could you think that little of yourself?” He walked over to the window and pushed the blinds aside slightly to look out to the parking lot below. “Sometimes when you say things like that, it drives me crazy that you don’t see yourself very clearly.” 

Castiel was befuddled. “What are you talking about?” 

“The way you talk about yourself.” Dean turned around. “Your job doesn’t define your worth, Cas. You could be a professional dumpster diver, and I’d still…” He stopped and cleared his throat, gaze skittering around. 

“You’d still what?” Castiel said to the empty air. 

Dean clenched his fists. “I’m sorry I came here. I’m sorry I intruded into your life. I’m so sorry for everything.” He quickly crossed the room and snatched up his jacket. He made it as far as the door when Castiel spoke. 

“That’s it? You’re just gonna leave?” It wasn’t the detached tone he was going for, but he couldn’t believe the universe was making him watch this man leave him again. He was lucky he was allowed to walk out first the first time around. This time, though. It was unbearable. 

“I don’t know what else to do.” Dean had his hand on the doorknob, about to turn it and walk out of his life forever. And still, he had the audacity to sound hurt and broken when he’d left Castiel in more pieces that he could try to pick up. 

“Yell at me, call me names. Something I can work with!” Castiel hated himself for the tears he could feel gathering. He was really that guy who was going to pout and cry because the man he wanted didn’t want him in return, and wasn’t putting up a fight or doing anything to save whatever scrap of something he thought they had. 

“I don’t want to yell at you or call you names.” Dean spoke calmly and without much inflection at all. “I came to see if you were happy. I won’t try to get in the way of that anymore.” He turned the knob. 

“I lied.” 

That made Dean stop finally. He glanced back, pain clear in his eyes. “About what?” 

“I’m—I’m not happy. I’m pretty fucking far from happy.” 

Dean worked his jaw for a few seconds, clearly working through things in his head. “What about Trevor? Looked like he was pretty thrilled—“

“Shut up. I’ve been miserable.” He might as well be honest. Dean thought he was making Castiel happy by leaving? What a fucking joke. “I almost didn’t go out with him at all. I haven’t been with anyone since I left. I can’t be with anybody else.” 

“Cas—“

He plowed on, ignoring Dean. “I tried to keep track of you in the news, you know? Kept an eye out for anything to do with the company or you or Sam. See if you’d had to liquidate everything, or… or were seeing someone new.” 

“I can’t be with anyone else, either, Cas. I’m miserable too.” Dean finally let go of the door and stepped towards Castiel. He approached like Castiel was a frightened animal and Castiel just wanted to press himself so tightly to Dean that they couldn’t separate again if they tried.

Castiel just launched himself at Dean. 

The tension in the room exploded as Dean caught his face in his strong hands and hauled him in close. It was messy and too wet, and Castiel was pretty sure their teeth were involved too much for it to be a proper kiss, but they kept as much contact as they could. Immediately, blinding heat was filling Castiel to the brim and then some. This was what he’d been missing, what he’d been craving like a heroin addict. He was addicted to Dean. He had been this entire time, and this was just getting his fix after too many months sober. Dean pressed his thumbs into the bolt of Castiel’s jaw to get him to open up, and he plunged his tongue inside like he wanted to crawl inside and never come out. Castiel’s hands were immediately at Dean’s waist, pushing his shirts out of the way to get to warm skin. Dean shivered and pressed closer, nipping at Castiel’s jaw, pulling breathless moans out of Castiel. Slowly, Castiel fought for some clarity. 

He pushed against Dean’s hard body to get some space to think. “Don’t. Don’t do this if you’re just going to leave me again.” 

Dean pulled away with kiss-bitten lips and his clothing rumpled. He looked like he’d just been hit over the head. “Cas, I never want to leave you.” 

Castiel clenched his hands in the fabric of Dean’s over shirt. “Bullshit. Why’d you let me drive out of that garage?” 

Dean stared at him for a second. “Okay, let’s just sit for a minute. Talk this out.” He pulled away fully from Castiel and took a breath, smoothing his hands over his clothes. He reached out a hand. Castiel only hesitated for a second before he took it, sliding his fingers between Dean’s blessedly warm ones. The rush beneath his skin quieted into something more manageable, and he allowed Dean to tow him back to the couch. 

When they were seated, Dean put a reasonable amount of space between them, though he visibly struggled with the distance. It seemed Castiel wasn’t the only one dealing with a dry spell. “Sam mentioned that there might be some confusion as to why I asked you to leave.” 

“You were pretty clear on that front.” 

Dean shook his head. “Let’s just walk through it. Okay? No confusion. Everything out on the table.” 

Castiel nodded. 

“You have to know, I’m not mad about the news story. At least, not at you. God, I couldn’t have cared less about the stupid news outlets after you left.”

“They were going to rake you through the mud.” 

He shrugged. “Maybe, but it wasn’t just me they hurt. Cas, you don’t know how many times I called some douche-y guy named _Balthazar_ of all people to get you back in to the Institute. I offered so much money, but they said they had no way to contact you anymore anyway.” 

Utterly confused again, Castiel said, “Why would you do that?” He couldn’t even begin to picture the conversation that must have gone down between his advisor and Dean. Balthazar pissed him off every single time they spoke, simply because of how the man lived; he couldn’t imagine Dean trying to navigate that on his own. 

“I wanted you to have what you wanted so badly. I couldn’t believe they’d dragged you down too.”

“You told me to leave town; I wouldn’t have gone back anyway.”  
Dean reached out and picked up his hand. He cradled it between his own hands, pleading clear in his eyes. “I was hoping against everything you’d ignore me and stay. I didn’t know where you’d gone. Had no clue.” 

Castiel snatched his hand back. He was angry and confused, and more than a little frustrated with how cryptic Dean was being. “Why do you keep trying? It was a business transaction, we knew that. A contract.” 

Dean’s face shifted. “Did you ever look in the glove box of the roadster?” 

Cas raised an eyebrow. “Yes. I took the money,” he said unapologetically. 

Waving him off, Dean continued. “Did you… happen to find an envelope?” 

Cas had thought it was the title to the car or something similar, so he hadn’t bothered with it. “I didn’t open it.” 

Dean nodded. “Can I borrow your keys a sec?” Castiel stood to grab them off the counter and tossed them to Dean, utterly nonplussed. Dean slipped out the door and thundered down the stairs. Castiel crossed his arms and sat down on the far side of the sofa. What a night this had turned out to be. 

Dean reappeared in less than two minutes, panting slightly and clutching the sealed envelope from the car’s glove compartment. He collapsed on the couch and thrust it towards Castiel, who took it hesitantly. 

“I never meant to give it to you like this, and I was terrified you’d read it after you left and just throw it away or burn it.” 

“What is it?” Castiel carefully slit the top of the envelope and pulled out a sheet of paper folded into thirds. The paper was heavy, professional grade. He turned it over and was greeted by the sight of a short paragraph of text followed by two signatures with a date of over six months ago. At the bottom was another signature with a date.

“Didn’t you read the last paragraph of the contract?” 

In truth, Castiel hadn’t. He’d been too caught up in not appearing too nervous, anticipating the kinds of things he’d be expected to do, and wondering if he would even enjoy working for the man currently sat on his second-hand sofa. His life had changed quite a lot in half a year. 

His eyes darted up to the paragraph listed above both their signatures and read. 

_This contract will become null and void with the utmost promptness if and when either party (Novak or Winchester) develops emotional commitment far outside what is considered reasonable and responsible for the above stated arrangement. Should such state be reached, either party (Novak or Winchester) may terminate the contract by signing on indicated line at the bottom of this document. Upon signing, all contracted obligations for both parties are negated in full with no risk of legal, emotional, or other repercussions._

Castiel’s gaze jumped to the bottom where Dean’s signature sat neatly with all it’s usual flair. To its right was the date it was signed. Exactly one day before Castiel left Chicago. 

He looked up at Dean, who was staring warily at him. “I don’t understand.” 

“If one of us signed that paper, the deal was off. No questions asked.” 

“So you signed it the day before I left?” 

“Yes.” 

Castiel hesitated. Things weren’t adding up. “I don’t get how this is supposed to make anything easier to understand.” 

“I signed it because I was done dealing.” Dean said, patiently. “I wanted to give you a choice. To keep what we had going, or do something else.” 

“Why didn’t you give it to me that day then? Why stick it in the glove box where I wasn’t going to find it?” 

Dean shrugged. “Like I said, I hadn’t ever meant to give it to you like this. I wanted the car to be a proper gift, and then I’d give you the envelope and…” 

“And I’d be free.” Even as he said the words, he couldn’t believe it. Could it be that he hadn’t been as alone as he’d felt in his feelings? He doesn’t want to wake up five minutes from now to the shrill sound of his alarm, to figure out this had only been a dream. He doesn’t know if he can handle having the memory of Dean saying everything he’d been aching to hear for the past five months turn into dust in front of him. He doesn’t know if he’d ever actually wake up from that dream. 

“And you could make your choice.” Dean pressed, clarifying. “To keep on as we were, or to do it for real. Or leave, I guess. If you were tired of me.” He chuckled, humorlessly. 

“You didn’t want me to leave?” Castiel clarified. 

“Cas—the last thing in the world I wanted was for you to leave. I’m dyin’ without you. I thought you couldn’t stand the sight of me.” 

Ridiculous. “Dean, you’re my favorite sight in the world.” 

“I got you kicked out of art school, Cas. It was your destiny. Money or not, that doesn’t exactly cause a lot of happy feelings towards a person.” Castiel was struck with how little Dean thought he deserved this. Maybe they were a better match than he’d thought.

Castiel squeezed his hand, reveling in the fact that he could. “I really have been miserable. I missed you so much I was seeing you in my dreams.” He probably should have felt bad admitting that, but it was freeing saying it to someone who wouldn’t offer to call the nearest psychiatrist for him. 

“You don’t know how weirdly glad it makes me feel that I wasn’t the only one. Never wanted to wake up.” Dean said with a smile. 

“So, as long as we’re communicating and everything… you don’t want me gone?” 

“No. I never want you gone.” 

“But you don’t want to pay me anymore?”

Dean backpedaled. “I mean, of course I’ll still pay for stuff. I don’t have all this money for nothing.” He paused. “I just… don’t want it to be why you’re around… if that makes sense.” 

“What if I still wanted to do sex work?” He was mostly teasing, he didn’t want to trick on dirty side streets for any longer if he didn’t have to. 

“That’s your decision, and no one else’s. Like I said, you could be a dumpster diver… and I’d still love you.” Dean locked eyes with him, even as the blush was covering his cheeks and threatening to take him down. 

Castiel’s heart swelled in his chest. “I love you too. Honest to God.” 

Dean gave him a helpless little smile and looked down at where their hands were twisting over themselves, clasping and unclasping. “Awesome.” He said quietly. 

“Actually, I was already half in love with you the first time you sucked me off.” 

Dean rolled his eyes and pulled away, standing to look around. “So this is Kansas. You sticking around here or can I convince you to come back to the Windy City?” 

Castiel stood as well, and all but wrapped himself around Dean. His heart was so full, and he was sure he was grinning deliriously. “I want to go home. With you. And Bobby and Missouri and the garage and everything else.” 

“Even my four living rooms?” Dean wrapped his arms around Castiel’s middle and squeezed him close.

“Especially that big couch in the main one we made out on that one time.” Castiel fell so fast and hard for this man, there was no doubt he wanted to stick around for the rest of his stupid life. And knowing he wasn’t alone in that feeling? Amazing. 

“And we’ll be together? For real? No contract?” 

“Almost like real people.” Castiel couldn’t help teasing.

This kiss was different than their first kiss of the evening. It was different than the very first kiss they had ever shared. It was different than any kiss they had ever shared in the course of the relationship. This time, when Dean leaned in close, Castiel didn’t feel like he was getting away with too much to be real sex work, and he didn’t feel like he was drowning in how lost he felt. In some ways, Dean knew him better than he knew himself, and he was more than happy to say that he knew Dean better than anyone else in others. 

“How soon can I get you under my roof again? More importantly, when can I get you into my bed again?” Castiel was happy to see Dean had gotten back his teasing edge. He’d missed it. Immensely. 

He shook his head. “So lewd. Immediately. Let’s leave tomorrow.” 

“Sounds great.” They kissed again, in the open air of Castiel’s borrowed living room. It was late, and the first real snow storm of the season threatened next week. The wallpaper was definitely peeling in some areas, and the dining room chairs were too mismatched to be anything but on purpose. And in the moment, Castiel didn’t want to be anywhere else. 

Except maybe one place. 

With a smack, Castiel pulled away. “Come on.” He stepped away and pulled Dean by the hand to the hallway. 

“Where are we going?” Dean asked curiously, going along all the same. 

“To bed. You drove ten hours today.”

“Cas, we don’t gotta rush anything. I can get a motel or something.” 

Castiel stopped to face him. “Dean, I’ve waited five months to put my hands down your pants again. Please don’t deny me any longer.” 

“Yes, sir.” Dean scooped Castiel’s feet up from underneath him and practically jogged to where Castiel’s bedroom door stood open. Castiel laughed the whole way and felt utterly weightless. The door slammed behind them, leaving the rest of the apartment in stillness.

**Notes for the Chapter:**

> THE PENULTIMATE INSTALLMENT. AAAHHHHHHHHHHHH.
> 
> You're almost there! If you've made it this far, be prepared for a last chapter full of fluff, smut, and (probably) some kissing. Who knows. 
> 
> Thanks for reading!   
> -azo


	20. Wind Up

**Summary for the Chapter:**

> The one where Anna is everyone who read this and wanted to take a swing at Dean for being a moron.

Castiel didn’t remember his mattress being this comfortable when they picked it up at a secondhand store, much to Anna’s dismay. _‘It could have BEDBUGS, Castiel.’_ He had been willing to take the risk for having his own bed in a very long time, however. Thankfully, it hadn’t had bedbugs or anything else untoward that would have put him off, and he happily covered it with sheets that he picked out at the local Walmart—an hour away—and relished the thought of falling into a soft place to call his own every night. 

Of course, when he bought it, he hadn’t exactly pictured falling into it clutching a handful of Dean Winchester’s shirt, but he’d deal. 

As soon as they’d burst through the doorway, however, Castiel was treated to a first-hand look at how comfortable his mattress really was when he was all but tackled onto it. He pulled Dean down with him, not willing to lose contact with him for even a second. Five months apart was too long. He wasn’t sure how he thought he could live without this. There was no denying Dean was all to able to actively _do things_ to Castiel, even in the time they’d spent away from each other. 

Dean’s lips were sweet and hot against his, and Castiel pressed himself closer, aching to be melded to the man above him. Dean must have felt the same pull, because he couldn’t seem to keep his hands in one place. He swept them all over Castiel’s body, from shoulder to hip, leaving what Castiel thought must have been scorch marks with the heat and tingles his hands left. “Missed you. Missed this.” Dean whispered against his lips, when they were free. “Missed you so much, goddamn Cas.” Castiel nibbled on Dean’s lower lip, really sinking his teeth in when Dean shoved his warm cock against his own. Dean gasped, all the air in his lungs leaving his body and filling up Castiel’s with so much light, he thought he might burst. 

“Do it again. Lemme feel you.” Castiel murmured back, his hands untwisting from Dean’s hair and sliding down to his hips. They were both still clothed, and if Castiel had his way, he’d take his damn time unwrapping his present in front of him. He slid his hands into Dean’s back pockets, grabbing himself a generous handhold and forcing Dean’s hips forward to grind into himself. Dean grunted in response and anchored his arms on either side of Castiel’s head. He pushed himself against Castiel in a clothed mimicry of what they both wanted desperately. Castiel cried out at the pressure against his cock and held on desperately. 

Dean pulled away from his lips and pressed hot kisses to Castiel’s cheek and down his jaw to nip at his earlobe. Dean’s breath was hot and humid against his ear and he closed his eyes against the growl that lit him up. “‘M gonna blow like a teenager. You make me wanna come so fuckin’ bad and we haven’t even done anything yet.” 

“Dean—!” Castiel was pinned, both by Dean’s words and his body slung so carelessly over his. He was trapped, completely unable to go anywhere, and utterly unwilling to be anyplace other than here. 

The grinding picked up, Dean was getting sloppy in his movements. Castiel opened his eyes and saw just how desperate Dean was, his expression probably a mirror of his own. They were both close, emotions too high to be anything but a hinderance to their lasting time. Castiel knew they could get a better angle, even for this dry humping that Castiel had absolutely never had so much fun doing before, but he didn’t want Dean’s heat to go anywhere that wasn’t draped all over him. Instead, he settled for pulling the hem of Dean’s shirt up, desperate to get to skin. He tugged it up until Dean got the message and pulled the scant millimeters away to throw it off and into a corner of the room. When he was bare from the waist up, Castiel clawed at his back, pulling Dean closer to him. Dean arched into the touch like some kind of cat, and attacked Castiel’s mouth with new fury. They were going so hard, the bed frame was squeaking, and the neighbors had to have heard something by now, but the only sounds Castiel could hear were the breathy gasps coming out of Dean’s mouth. Dean had always been vocal in bed, spouting enough dirty talk to curl Castiel’s toes, but he wasn’t one for errant noise. This was the sound of Dean being completely out of his own control, brought to the brink of desperation from absence, longing, and anticipation. 

Castiel’s hands wandered back up to Dean’s face, brushing back his sweaty hair and tracing across his cheekbones. He spread his legs more so Dean had no choice but to fall further into him. He shushed Dean, internally thrilling to the raw want in his eyes. “Come on, Dean. Come for me.”

“Cas…” Dean whined, leaning forward to kiss him again. Castiel moved out of the way just enough so that his lips his cheek. Dean buried his face in Castiel’s neck. 

“Keep going, you’re really close, aren’t you?” Castiel asked with a smile. Dean nodded furiously in the crook of his neck. “Come for me and we can go again. I really wanna get your cock inside me tonight.” 

It was enough to set Dean off, freezing for a second before he started shuddering all over. Castiel came to the feeling of wet heat against his cock as Dean spilled his release inside his boxers. Castiel might have thought about giving him shit for it, but as he thrust his hips into the good feeling, he wasn’t any better off. 

Dean peppered little kisses all over his face and neck as they both calmed down. After a while, he slung himself to the side and draped an arm over Castiel’s chest. Castiel immediately scooted closer, sure of his welcome now, and nosed at the side of Dean’s face until he turned to let Castiel kiss him. 

“That was fuckin’ embarrassing.” Dean grinned despite himself, his eyes closed against the onslaught of Castiel’s kisses. 

Castiel nudged him. “No it wasn’t. It was great. I missed this.” 

“I don’t think I’ve went off that fast in at least a decade. Maybe more.” 

Something occurred to Castiel and he pulled back. “Dean, how old are you?” 

Dean opened his eyes. “I’m thirty.” 

Castiel paused. “I never thought to ask. I know your birthday’s in January… I just never knew how old you were.” 

“Having second thoughts about shacking up with an old man?” Dean nudged him like he was teasing, but Castiel was so well-versed in Dean’s vernacular by now that he caught the slight edge of worry. 

He turned so he was on his side, and tugged Dean to face him, their noses so close they were practically touching. “Never.” He whispered. 

Dean smiled. 

After what could have been a few minutes, but felt like hours or even full lifetimes to Castiel, Dean sat up and spoke again. 

“So. There’s something I want to discuss with you. And I know this is probably the worst timing ever, but—“

Castiel groaned with the effort of pushing himself to sitting and cut him off. “You’re not proposing, are you?”

“No! No, that’s a whole other conversation, and I think we need some time before we even consider that—“ 

“Dean—“

“It’s just something you said before and it was probably just in the heat of the moment and everything, but I have to know—“

Castiel sighed and put him out of his misery. “Dean, will you fuck me?” 

The man opposite him apparently ran out of steam in a huff. “I—yes. That.” 

“I meant it, you know. I’m ready.” He reached out and took Dean’s hand, who gave it eagerly. Dean’s thumb stroked over his, sending wayward sparks skittering over his skin. 

“Are you sure, though? We got nothin’ but time. I don’t mind waiting.” 

“I know you don’t. That’s why I’m ready.” 

Dean smiled helplessly down at their hands for a moment. “I promise I’ll take real good care of you.” 

“I know you will. I have lube and condoms.” Castiel jabbed a thumb over his shoulder to the bathroom. 

“Thought you were gonna get lucky on your date?” Dean raised an eyebrow teasingly. 

Castiel smiled. “No, honestly they’re Anna’s, but I’ll buy her new ones.” 

“Thank god she’s prepared then.” 

“Come here, Mr. Winchester.” Castiel reached out and grabbed his bicep, using it to pull the man closer. 

Suddenly, a bang sounded from the living room. The pair jumped apart, startled. Dean leapt off the bed and edged towards the door, one hand extended towards Castiel urging him to stay in place. 

The voice from the living room sounded female, familiar, and somewhere between pissed and excited. “Castiel, I know there’s a good chance you might be naked with my dance instructor, but you have _got_ to come see this—!” 

Dean and Castiel glanced at each other. Castiel couldn’t help but laugh with bewilderment. 

“Anna.” For a brief moment, Castiel considered pretending not to be home.

“Should I be worried?” A frantic knocking on the door rattled the hinges slightly. Dean glanced between the doorknob and Castiel like he actually wanted an answer. His tousled appearance made him a bit better fitting into the makeshift shelter the apartment had turned into, but his face still made Castiel wish for better lighting and softer linens. 

Anna’s voice sounded again, like she had pressed her face against the door, just short of coming in and disturbing their illusion of alone time. “Castiel! Put some pants on! You won’t believe who’s in the parking lot!” 

Chuckling, Castiel threw his legs over the side of the bed, straightening out his clothes as best he could. When he looked less like he had been scaling Fuck Mountain for the past three hours, he crossed the room and stood in front of Dean, with his hand on the doorknob. “Should you be worried about meeting Anna? Definitely. Still up for it or do you want to make a quick escape?” 

Dean ran his hand through his hair and cracked a joint in his spine. “I can handle roommates. Piece of cake.”

Castiel raised an eyebrow. Dean pushed past Castiel, and opened the door. 

He only got one step out of the room, before Castiel heard an enraged female cry of "What the fuck are _you_ doing here?" followed by a resounding _SMACK!_ and Dean Winchester, billionaire entrepreneur and the All-American poster boy for Midwestern living, was on the ground.

… 

To say that Anna was less than thrilled about meeting the man that broke her best friend’s heart was… overestimating the extent of her feelings by about three astronomical units. She crossed her arms and fixed the man with a glare so hot, she felt she could have melted through several solid steel walls. Standing there in the doorway of Castiel’s bedroom with his shirt off and pants unzipped and rumpled was the man Anna had wished every plague and misfortune the second she got a phone call from Castiel at that gas station outside of the city. By the way Castiel had cried in her lap that night, she wished neither of them would ever have to see this man again. And here he was, clutching his cheek and cowering behind Castiel, whose hair looked fucked up enough to clearly illustrate that this was not a social call. 

Really, hitting him had not been her first choice, but she had a tendency to take openings where she could find him, and Dean Winchester had a _very_ punchable face. It wouldn't bruise. Probably.

“Dean Winchester.” She tipped her chin up. 

The man glanced around uneasily for a second, before stepping around Castiel again, hesitating the entire way in case he'd have to duck for round two. “Miss Anna Milton, I assume.” He stuck out his hand.

Anna had to give Castiel some credit, this man was handsome. Anna had flipped on a few lights when she came in, hoping against hope she wouldn’t see any naked male ass in her living room, especially her roommate’s, and she could see just how pretty Winchester’s face was. He was tall with broad shoulders, full lips and a strong nose, balanced with an even stronger jaw. And those eyes were _some_ kind of green. The man’s forehead creased when Anna didn’t meet his hand with hers. He awkwardly pulled it back and glanced back at Castiel. 

Castiel pushed past the both of them into the living room. He tugged Anna’s arm until she followed him to the couch where he sat down, pulling her with him. Winchester sat a reasonably safe distance away from the pair on one of the armchairs. Anna kept her eyes on the familiar stranger in her apartment the whole time. 

“So, you were yelling about something when you came in.” Castiel prodded her for attention. 

Unwillingly, Anna shifted her eyes to her roommate. “Well, I know I promised to stay away for your date tonight, but I was on my way to Salem’s house and wouldn’t you imagine my surprise,” she glared at Winchester again, “when the person I never thought would darken your doorstep again has their big _obnoxious_ car outside our building?” 

“You know my car?” Winchester asked, and Anna would say he almost sounded impressed. 

She sneered. “Everyone knows your car, Winchester. You’re the only billionaire in Chicago who drives something so—“ 

“Okay, alright, _anyway_ —“ Castiel interrupted, hands out placatingly, “Yes, I can see how that might be a bit of a shock—“ 

Anna continued, gathering steam again. “—and then not only do I find him in our parking lot, but also he’s in our apartment? In your bedroom? I thought you were out with Trevor?” 

Castiel glanced at Winchester. Anna stood then and paced between the couch and the bookcase against the wall. “And another thing, why is he even here? After what he put you through— what the news said about you…” She turned to Winchester. “Who do you think you are?” 

Anna would have smiled at the way Winchester seemed to cower at her words if she weren’t so blazingly angry. One of the richest men in the entire city of Chicago, and he was afraid of angry women. 

Castiel got up and pressed himself into Anna’s space, pushing her back a few steps from where she surely would have pounced on Winchester. “Anna, it’s okay. It’s all okay. He came to apologize and talk about—“ 

“He drove you out! Got you kicked out—“

“Anna—“ 

“—if it was me in this situation—“ 

“I think that’s a little—“ 

Anna turned her accusing finger to her best friend, “Don’t you dare tell me it’s different Castiel Novak, you know that’s a heap of bullshit—“

“You’re right.” Winchester finally spoke up. 

Castiel sighed. “Dean—“ 

Holding up a hand gently, Winchester stood slowly. “She’s right, Cas. I got— I got a lot to answer for. I know it.” He looked pleadingly at Castiel. 

Anna gestured wildly and turned to look at Castiel too, like ‘See?’ 

“Look, I know I got no right,” Winchester started, “But would it be too much to ask to talk to Anna for a second?” 

Castiel’s gaze darted between the two of them. Anna felt her eyebrows hit her hairline. Winchester wanted to talk to her? Maybe to tell her he was taking Castiel away no matter what she thought. Maybe to threaten her for talking so imprudently to him. Maybe to tell her she’d never work in this town again in some kind of Godfather-esque scene. She curled a lip and tried to remember where she left her butterfly knife. 

Sighing, Castiel put down his hands. “Anna?” 

She stared at Winchester for a moment longer. “Fine.” 

Castiel huffed. “Well, I guess I’ll go get a soda or something. Call me when you’re… done or whatever.” He paused by the chair where Winchester still sat, smiling gently when Winchester ran his fingers over his knuckles. They shared a look, clearly communicating in some unspoken thing inaudible to anyone outside their tense little bubble. Anna rolled her eyes and looked away. That wasn’t meant for her eyes. Castiel grabbed his shoes and coat from beside the door and left, gently closing the door behind him and starting down the stairs. Anna was left with Winchester all alone in her apartment. 

"You got a hell of a right hook." Winchester smiled, but touched his cheek where it must still be tender. 

Anna rolled her eyes. "Just know that I'm actually a southpaw, so you got off easy." She grinned feral when Winchester winced.

Winchester leaned forward. “I know you’d love to yell at me, and believe me—I know I deserve it.” Anna scoffed, but fell silent when Dean nodded and looked down self-depreciatingly. “But I’d actually really like to just… talk if we could. Straighten some things out.” 

“You want my blessing.” Anna thought it was rather poetic. She supposed she was one of the closest things Castiel had to actual blood-relatives anymore. Most of his surviving family was in Illinois, but he neither spoke of them, nor seemed to care about their wellbeing. It seemed almost fitting that the man vying for Castiel’s hand would go through her. No matter how ill-advised and stupid it was for him to try. 

Dean shrugged. “I want to make sure that if—by some miracle—Castiel wants to be with me, he isn’t leaving his friends behind angry. If there’s one thing I’ve learned in my life, it’s that everyone needs someone on their side. The more people the better, really.” 

“And just why would I be angry or even mildly upset that Castiel is being an idiot and going back to you?” She asked, venom in her tone. “You weren’t there. You didn’t have to scrape up the pieces and listen to him cry over you.” 

“Look. You’re his best friend in the world. I know that. He looks out for you just like I know you’re looking out for him.”

“So you get why I’m mad?” Anna was several miles past mad, but she didn't really want to start screaming this late at night in a town this small.

“I definitely get it. If I wasn’t such a greedy bastard myself, I wouldn’t even dare to put Castiel through this.” 

“Then why are you here? If you care so much, you’d let him move on, Winchester.” 

“Call me Dean.” The poor bastard actually thought turning up the charm would win him some points. 

“Dean, you broke his heart. It might have been just a job for you, and maybe it started out that way for him, but…” 

“But something changed,” Winchester—Dean finished. “I know, believe me. It was only a job for maybe twenty minutes. An hour tops. I knew he was different right away.” 

Anna narrowed her eyes. “What do you mean?” 

“It wasn’t just a job for me either.” 

That made Anna still. She had known from the get-go that this was a different sort of job than Castiel’s usual. He’d been more flustered about it, more secretive. Like he wanted to keep it for himself. He’d been… happier, though. Lighter. “Kinda late to be figuring that out, isn’t it? We left months ago.” 

Dean looked down at his hands. “That’s where the misunderstanding part comes in. I didn’t really want him to go.” 

Screw it, Anna was curious. “Then why send him away? Castiel wasn’t making a whole lot of sense that day, but he was pretty clear on that. You didn’t want him there.” 

“I didn’t want him hurt!” Dean burst out. “I know this is hard to believe—and trust me, if I were in your shoes, I wouldn’t want any asshole who upset Cas to even come near him. But just know that when I say I regret these past five months more than anything I’ve ever done in my life, I mean it.” 

Anna tilted her head in thought, assessing Dean. He seemed genuine. But if she’d learned anything on the streets of Chicago, it was how to seem convincing. “You know why I can’t trust whatever bullshit story comes out of your mouth, don’t you?” 

“I know—“

She plowed on, not giving him a chance to speak. “And you know that Castiel and I would die for each other, because we keep each other safe, right? That’s how the rest of us survive when we don’t have the rest of the one percent backing us up. We have to make friends and survive.” 

“I get it, I—“

“And you _know_ … that Castiel is my best friend in the world?” She hoped she wouldn’t scare off Castiel’s flame.

Dean was silent with a pained expression. Waiting. 

“And I want him to be happy. And even though I can admit that I don’t trust you or particularly like you, I have to say that he was… happier with you.” Anna finished. 

The man in her living room folded his hands and smiled down at them. 

Anna let the moment hang. She started again, quieter. “I think what I’m really struggling with is the fact that I don’t know you. I’ve seen you on TV, I googled you to see what your weirdo company actually does—apart from the salacious news stories, and you seem like an upstanding guy.” She made sure to look at him straight in the eye. “But I can’t trust that. Not when you left my best friend broken.” 

Dean nodded and opened his hands, palms up. “How can I make this better?” 

Anna crossed her arms and regarded him for a moment. She didn’t really know how to phrase what she wanted into a sentence or if she even had any right to want what she wanted, so she asked a different question. “Are you taking Castiel with you?”

“If he wants to come back with me, I’d love to have him.” Anna had to admit that Dean had the genuine thing in spades. She believed him. 

“And if he doesn’t?” 

“Then I’ll deal.” Dean answered immediately. 

She paused again. “Did he forgive you?” 

“I hope so. I’d grovel on my knees for the rest of my life if I had to.” 

Anna uncrossed her arms and sat on the couch across from Dean. “You care about him, don’t you? Like, for real?” 

“I love him.” 

“Does he know?” She asked. Dean opened his mouth and glanced around uneasily. “Sorry, that’s personal.” He shrugged, but chose not to answer. In all fairness, she really did not want to know the finer points of Castiel’s love life. “Just promise me you aren’t going to keep him locked away in that huge-ass fortress of yours.” 

“No, I swear. If he lets me, he’s getting a first-class ticket back into that art school of his—even with that douchebag _Balthazar_ —“ 

“Oh, you met Dr. Reynolds, then?” Anna asked, grinning. She could only imagine how that conversation must have gone. 

Dean scoffed. “Pretty sure his office blocked my calls after the sixth call.” 

“I like you, Dean. Well, that’s not entirely true, but I like you more than when I found you here.” 

A smile stole across Dean’s handsome face. “Likewise, Anna. I’m still terrified of you, but… I can see why Cas likes you.” 

“Good. Keep it that way.” 

“Can I interest you in a ticket back to Chi-Town?” 

Anna stood again and went to retrieve her bag from where she dropped it when she entered the apartment. “Nah, I’m starting something here, I can feel it.” She pulled out her dance gear and tossed it in the laundry basket sitting near the kitchen. They’d have to drive down to the laundromat in a few days. She turned back to Dean. “I’d like to visit, though. If you can bear letting Castiel out of bed for a while. He promised he’d come see me in the Gala at the end of April. It’s when we graduate. Well—when I graduate, I guess we’ll see where Castiel is at in terms of credits.” 

Dean looked thoughtful. “Right, the Gala… little over four months away. What would a painting major need to get a spot?” 

Pursing her lips, Anna considered. “Probably just needs a piece ready to show for finals. Maybe more if he really wants to make an impression on the professors. And a place in the program, obviously.” She paused. “What are you planning, Winchester?” She had a feeling she already knew. 

Dean smiled, and Anna grinned in return.

**Notes for the Chapter:**

> Happy last day of June! If you're playing along at home, you might notice this story got extended for one more chapter. That is because I'm a wordy bitch who can't tie up a story to save her life. There's still so much to do. Stay tuned, I guess. 
> 
> Thanks for reading!  
> -azo


	21. Love in Stereo

**Summary for the Chapter:**

> All things must come to an end.

In the end, they only would up making it to Dean’s bedroom because Anna wanted a ride back to Chicago. She wasn’t staying—her life in small-town Kansas too fulfilling—but she wanted to grab a few things before heading back; this time with Jo in tow. They arrived at the house in record time, and stopped only briefly to say hello to Missouri in the kitchen, the housekeeper insisting on a hug while they were quite literally tugging each other out of the room. 

The bedroom door slammed in the same second that Castiel’s back hit the mattress, and he felt himself sink into the memory foam like an old friend. Dean followed soon after, caging him in. They were pressed together as much as they could, Dean’s hands going to his face and stroking across his cheekbones. 

“Heya handsome.” Dean whispered.

“Hello, Dean.” Castiel breathed back, the world outside of their private room already forgotten. “Are you gonna fuck me?” 

Dean chuckled. “No, I’m gonna make love to you on this bed. And then I’m gonna do it again.”

“And again, and again, and over and over?” Castiel couldn’t help but grin. 

“Until we die, baby,” Dean finished, pressing his lips to Castiel’s. 

From there, Castiel’s awareness focused on bits and pieces of the experience, too caught up in the heady lust between the two of them to stay tuned in for long. Dean’s tongue swiping across his chest, his own hand pressed to the sheets by Dean’s strong fingers, thrusting upwards into Dean’s heat and hearing both of their breathing stutter. 

Dean worked lower and lower on his body, the tension ramping up every inch closer he got to the place Castiel wanted him so desperately. Dean sank down on Castiel’s cock, his tongue laving over the slit and down, down, down. He pulled off, only to suck one of his own fingers in his mouth, getting it wet enough that it shone in the pale moonlight coming from the wide windows. 

“You ready, angel?” Dean asked softly. 

“Put it in me, Dean.” Castiel replied, breathless.

Dean’s mouth quirked up and he slipped his finger in Castiel’s hole at the same time he took Castiel’s cock in again. Castiel felt his eyes roll back as he was filled, ecstasy but nowhere near enough. It wasn’t long before he heard himself chanting, “more, more Dean, more!” Dean surfaced again, looking as fucked out as Castiel felt. 

“You sure you’re ready?” 

Castiel smacked his hand at the bedside table until he was able to open the drawer. He fished around blind until he found the small bottle he knew was in there. He all but threw it at Dean’s head, which caused Dean to laugh. 

“Fuck me, hot shot.” Castiel ground out. 

Dean smacked a kiss to his hipbone. “Gladly, baby. Tell me if it’s too much.” 

“I will.” Castiel promised. 

Dean pulled back, opening the tube with a slowness that had Castiel nearly clawing his face over. He held Castiel’s gaze as it dripped over his fingers, rubbing it into the whorls of his fingertips. “I want you to know that I’ve been waiting for this moment since I first saw you in that dive. But I’m so glad it’s now instead of then.” 

Castiel gasped. “Dean—“ He reached out a hand for him, feeling lead in his arms with the anticipation warring with his utter contentment to stay where he was. Dean took pity on him and leaned down to kiss him, slipping his tongue into Castiel’s mouth like he owned the place. 

Feeling a cold touch at his hip, Castiel jumped slightly, but was instantly soothed by Dean’s warm palm sliding over his skin. Two fingers pressed at his hole, stretching him bit by bit. He pressed lush kisses to Dean’s mouth, to his neck, his jaw, anything he could reach. Dean was practically purring. With fingers scissoring inside him, Castiel tried to imagine how it would feel—to finally have Dean inside him. For real this time. 

Dean ground up on his prostate, causing him to see stars and his legs spread even more. Castiel grunted as Dean suddenly pulled out. He sounded shaky. “Cas—you ready, darlin’? Ready for me?” 

Castiel hooked his ankles around Dean’s back and tugged him forward. “Inside... now.” 

Dean closed his eyes briefly, before taking his cock in hand and spreading a liberal amount of lube across his skin. He lined himself up against Castiel’s entrance and pushed enough that the tip sunk in cleanly. Castiel was robbed of his breath again, and Dean’s arms were shaking minutely when he readjusted to stay balanced. Castiel reached up to twine his fingers around Dean’s wrists, tourniquets of their own right. 

“All the way, Dean.” 

Dean shuddered all over and thrust forward, sinking all the way inside in one thrust. Castiel tossed his head back, and found paradise. 

...

Castiel smoothed his lapel as he looked in the mirror, grimacing at how visible the tremor in his fingers was. He worked the knot of his tie loose for what felt like the millionth time, and fumbled it so it laid flat against his chest. The end of the blue silk fell limp when his sweaty hands released the fabric again, hopeless. 

He took a deep breath, and focused on his reflection. Really, the tie was not the most important part of the evening here. Having a tie would not make or break his performance. Still... it would be nice to complete a single task without his hands shaking uncontrollably. He stepped closer, and narrowed his eyes, resolute to his task. End over end, pull the thick side up so it went under the band... no, wait... try again, end over end—fuck. 

Blessedly warm hands landed on his shoulders, prompting only the tiniest of jumps, and then smoothed down his lapel to take the slightly damp fabric from his grip. 

“Easy there, Belushi. Don’t wrinkle it before I’ve even had a chance to pull you around with it.” Dean grinned easily at Castiel in the mirror, even winking at Castiel’s wry smile. 

“I feel even more uncultured than usual, not being able to tie a tie correctly.” 

Dean shrugged. “Takes time for anybody to learn. Here—“ He leaned down slightly so he was draped over Castiel’s back. He picked up either end of the tie, and within seconds, had a perfectly even triangle knot that laid flat against Castiel’s throat. Not too tight to choke him uncomfortably, but just snug enough to pull the collar of his shirt close to his skin to hide the hickey just barely visible there. 

Castiel admired his appearance and pulled the jacket straight again. “I see why you spend so much on tailoring now. My shoulders have never looked this broad.”

Smacking a wet kiss to Castiel’s cheek, Dean pulled away. “I used to hate it—getting all fussy over clothes. It does make a difference though. You look great. Delectable, I might even say.” 

Castiel turned away from the mirror, stepping in close to Dean’s personal space. He felt comfortable here. Welcome. “Thanks. You look nice too.” He paused for a moment. “What if this doesn’t work? I mean—what if nobody... nobody shows up or even...?” 

Dean gripped his shoulders again. “Cas, don’t stress yourself out with what you can’t possibly know. I can already tell you, people will show up. They’ve been lining up at the door for almost an hour now.” 

“Jesus Christ, really? They’re going to be disappointed then, I mean—my work is alright, but I’m not even enrolled at the Institute anymore. I’m a nobody—“ 

“Stop. You are not a nobody. You’ve got great references, and it’s not like you were a slouch when you were at school. It’ll be fine. Okay? Breathe.” Dean squeezed Castiel’s arms, dramatically breathing in himself. It was clear that Castiel was meant to mimic him. “You’re an artist, and this is just a showing. This is what artists do.” 

“Do you know that Van Gogh only sold one painting when he was alive? It wasn’t even his best one. No one appreciated him while he was breathing—“

“—and you’re gonna go the exact same way if you don’t calm down.” Dean said, exasperated, but smiling. “I don’t know if I should give you a blowjob or a bag to breathe into. Seriously. It’ll be fine.”

“But what if—“

“Nope. We’re gonna go out there, and you’re gonna talk to people who want to ask you questions, and you’re gonna be the most charming guy out there.” 

“I’m gonna puke if I try to talk.” 

“No, you won’t.”

“Yes, I will.”

“Cas.”

“No, don’t Cas me, Dean Winchester. You don’t know me, don’t presume to tell me what I will and will not—oof!” Castiel was cut off when Dean’s lips landed firmly on his own, his hands immediately going to the bolt of Castiel’s jaw, willing him to give Dean’s tongue space to work. 

“Guess we picked the dirty route then.” He muttered around the tangling of their tongues. “Better pipe down and open up, baby. You’re gonna relax if it kills me.” He grabbed Castiel’s face and forced his mouth open, plunging inside him. Castiel’s eyes opened, despite the closeness. The heat between them was stifling, and he couldn’t bear missing a moment. Dean met his gaze without fear, brow quirking in mirth as he ruthlessly fucked Castiel’s mouth with his tongue. 

Castiel grunted as he was pushed back towards the chair from Dean’s desk, unused for anything resembling business in this portion of the house. It was a rickety thing, creaky frame and a rough seat with a rougher cushion. Dean expertly grabbed it from its space underneath the wooden credenza and twisted it so it sat in the center of their room. He knocked Castiel’s feet out from under him, causing him to collapse into the seat with a grunt. When he landed, he scrambled to sit up better, but was thrown off balance by Dean roughly pushing his knees apart to make room for himself. The fly of his trousers was all but torn down, the flaps of expensive fabric pushed aside to make room for the ever-growing bulge in his underwear. As Dean freed his cock to the open air and tasted the liquid pearling up from the tip, Castiel inhaled sharply. “—Dean!”

Dean shushed him soothingly—if slightly condescendingly—and took him deep down his throat, down to the root. 

Castiel fell back with a soft _thump!_ on the back of the chair, and he would have tipped the whole thing over backwards if Dean hadn’t caught his ankle and yanked him back down, his head going with the motion enough so as to not gag himself. Castiel was pretty sure he was already seeing stars, but the way Dean started sucking nearly made the galaxies behind his eyelids explode in a new Creation. Universes were born, stars burst into life, only to be sucked back into death just as quickly. Castiel keened under the attention, pressed his thighs to the solid weight of Dean between them. He kept a hand pressed at Dean’s shoulder, either to urge him on or slow him down, he didn’t know. 

He babbled. He wasn’t aware of much that came out, but what he could piece together would have made him damn proud if the situation was reversed and he was servicing Dean.

Suddenly, Dean went lower, tonguing over his balls, following the line of smooth skin all the way back to his hole. He stiffened under the kitten licks Dean paid him, and buried one hand in Dean’s hair while the other one gripped the edge of the seat so hard, he was sure he’d damage it. The tongue underneath him flicked filthily, dipping in, swirling around, and teasing its way back out again. 

“Can I put a finger in?” Dean asked, somehow sounding smug while gasping for air. 

“You can do whatever you fuckin’ want.” Castiel managed to string enough brain cells together to answer. 

Dean tutted. “Easy, angel. Don’t let me get greedy.” He chuckled when Castiel thumped him on the head. “Maybe we’ll just speed things along, then.” 

Castiel had just about gotten his breath back in the pause Dean had taken, when it was stolen from him again. Dean fit his hands underneath Castiel’s thighs and lifted him so effortlessly, Castiel almost felt the beat of wings behind them balancing their weight. Dean shifted their positions so Dean sat heavily in the chair with Castiel clinging to him. 

“You think this is going to speed things along?”

“Don’t care if you jizz on my suit—I got ten more in the closet,” Dean said breathlessly, pulling Castiel in to kiss again. “You look—“ he grabbed Castiel’s ass and hauled him closer so they rubbed mercilessly against each other. Castiel wasn’t even sure when Dean had unzipped himself, “—too damn hot in your suit to ruin it, though. Gotta savor this moment.” 

Sweat was pouring off both of them. Castiel wasn’t convinced they’d have to burn both their suits after this just because of the sheer amount of bodily fluids on them now. They ground against each other, pressing and pulling, fitting their mouths together when they weren’t gasping for air. Castiel kept one hand soldered to Dean’s chest, just where his heart sat, feeling how it pounded and echoed the beat of his own heart, their bodies synced up in every way. They were just grinding, they both knew it. They weren’t trying to move forward, try to move into something that needed two times more room and ten times more prep, but they chased after each other. Castiel felt Dean’s hand creep up between his shoulder blades, hooking him a little more down while the rest of Dean pressed up. He felt utterly safe and possessed here in their private corner of Dean’s bedroom. Castiel pulled Dean’s hand from where it was plastered to his neck and held it in his. He brought it to his lips and kissed each digit, slipping his lips around the middle finger. He delighted in the way the green of Dean’s iris disappeared just a little impossible bit more as his nostrils flared and the arousal kicked up another notch. 

Dean shifted as he hooked his ankles around the legs of the chair. The wood underneath them both creaked in a worrisome way, but neither man noticed. “Gonna be late to your own fuckin’ party.” He breathed. 

“I’m the artist, we do that.” Castiel gasped back. He was so close, he was getting desperate. Desperate to have something fill him where he was aching, desperate to make Dean cry out like he had in the bed for their first real time when they got back from Kansas. He went down on Dean’s middle finger again, the tip bumping the back of his throat. He sucked as hard as he could when Dean’s big hand slipped across Castiel’s ass and played lightly over his hole again. It was enough to send him over the edge, and he pressed as close as he could, feeling Dean crawl out of his skin with need as well. Dean ripped his hand away from Castiel’s mouth as he crested, replacing it with his tongue. He clutched Castiel closer, hugging him tightly to his chest as their cocks spurted together between them. 

They came down slowly, sliding together like liquid and melting in a messy pile on the chair. It creaked and settled, protesting the weight of two grown men carelessly frotting each other, but held as they sat back. Dean stroked his fingers up and down Castiel’s spine, his touch whisper soft after the hectic pace they’d set earlier. They stayed there as their skin cooled and turned sticky. They stayed there and listened to the door down many hallways opened and closed repeatedly as guests entered the house and had loud conversations with each other amongst the colorful walls of artwork. 

Finally, when Missouri came and tapped at their door with a knowing “Make yourselves decent for your guests”, they ducked out of the chair with guilty smiles and went about getting re-fixed to go out in public. 

Dean had to change his suit. Castiel had to have Dean retie his tie. 

...

“I noticed they’re all the same.” Castiel looked around at where he was staring at the demon eye piece. Inky black stood out against the pale flesh surrounding the eye in the painting. There was no discernible iris, but the pupil managed to suck the viewer in even deeper than the sclera. They were all eyes. All twenty-three pieces in various but strategic locations around the “public” part of Dean’s house. The event attracted a lot of media attention, mostly because it was being staged by the reclusive billionaire by the lake, but already it was garnering it’s own. 

“Same?” Castiel was joined by a very pretty woman, a bit shorter than him. She had huge hazel eyes and a mischievous looking pout. 

“The eyes, they’re all of the same person. Just in different colors and designs.” Each piece was an eye or a set of eyes. Some were huge floor to ceiling pieces, casting baleful gazes over their viewers. Some were smaller, more intimate peeks into life, all in swirling eddies of bright greens, blues, yellows, and scarlets. Dean’s favorite was a tie between the original piece Castiel had painted for him, the only piece with no price tag on it as it was headed back to its permanent home in the garage after the show, and the huge piece Dean said looked like a merman or Davy Jones, the skin around the eye clustered with shells and barnacles, the fury of the ocean obvious in the color palette. Castiel’s favorite piece was this one in front of him—the demon eye he called Azaezel in memory of the client who started him on his path of depravity, but also into his new life. 

Castiel nodded slowly. “Yes, I wanted the focus to be on the mood, rather than the person himself. Sort of like a template.” 

“It’s all incredible work. You use the color blue like a weapon.” 

Castiel had never been told that before, and he was pretty sure it was a compliment. “Thank you...?” 

“Correct me if I’m wrong, but your appearance gives you away a bit. You’re very young to be wielding so much talent.” 

“Thank you, again. I uh... just finished at the Art Institute here in Chicago.” 

“Finished or graduated?” 

Castiel’s blood ran cold. He glanced at the woman. Her hazel eyes were lifted at the side like a wolf’s. “Just finished. Came close to graduating, but... maybe some day.” 

She nodded thoughtfully. “I don’t mean to pry, of course. Just that, I know sometimes school isn’t what makes people happy, you know? Not everyone is cut out to learn in a classroom.” 

“More people will tell you it’s the promise of what happens after the classroom, though, that makes it worth it. Hoops to jump through to make the right people happy.” 

The woman shrugged. “But if it doesn’t end up the way you wanted it to, does it make the suffering any more worth it?”

Castiel stared.

The woman bounced her eyebrows and turned back towards the painting. “Forgive me, that’s not why I’m here. This piece is amazing. Is it a...?”

“Demon actually. For when you need to confront the things that make you unhappy.” 

Silence fell between the two of them as they stared. Castiel felt shaken up to be sharing such a strange moment with a guest at his very own art show. He never thought he’d get a moment like this for his own. 

“Where do you get your inspiration, do you think?” The dark haired woman asked, no falseness about her enthusiasm. Castiel was glad to talk with someone genuinely interested in his work, without being driven by grades, contempt, or desire to put him on his knees. He didn’t know her name or anything outside this strange encounter, but she looked vaguely familiar and clearly had an interest in art.

“Unfortunately, I don’t have a good answer to that. I’ve always drawn eyes. This was more of an exploration of color and gradient in that form. I’m sure somewhere, there are papers from my first grade classroom absolutely covered in doodles of eyes.” Castiel smiled ruefully at her. 

Still, she smiled, simultaneously charmed and charming. “I’m sure that was a surprise for your teacher.” 

Castiel chuckled and agreed. He unwillingly excused himself when he saw a terribly familiar blond pompadour lingering by the piece he’d done for Dean, proudly hung up across the mantle like a proud parent might treat a refrigerator door. 

“Balth—Dr. Reynolds?” The man turned around, eyebrows hitting his hairline. 

“Mr. Novak. I must say, we were... surprised to say the very least when the invitation came in, but I have to thank you for your kind remembrance of the program.” 

“I didn’t invite you.” Castiel saw no need to mince words. He took a sick sort of satisfaction when Balthazar’s face dropped minutely. 

The professor pressed on. “In any case, I wanted to extend my congratulations on such a successful opening. Of course, one cannot always assume success based on sheer numbers, but you know that. Your real test will come with the sales afterwards.” 

“I know.” Castiel said coldly. 

“And I hope you’ll remember the department that helped you along when you are paying out your dues afterwards—“

“You’re asking for money?”

“To put it in such crude terms, I suppose. Surely you must see the etiquette of doing so, Mr. Novak?” 

“Dr. Reynolds, glad to see you got my invitation.” A voice sounded behind Castiel. He felt slightly numb as Dean’s hand rubbed his shoulder. 

“Mr. Winchester, glad to put a face to a voice on the phone.” Castiel recognized the put-upon falsely cheery voice Balthazar adopted when his present company could help him out financially. 

Dean extended a hand, ever polite. “Wouldn’t want you to miss this, after all.” 

“Yes, well. When Mr. Dean Winchester calls and says he has the finest private collection available and wants to show it off, who can say no?” Balthazar laughs humorlessly. “Of course, I was a bit surprised at your choice of artist, given... past events.”

“Oh, you mean that media attention all those months ago!” Dean laughed with ice in his smile. “What a misunderstanding that was. Completely got the wrong angle, didn’t they, Cas?” He turned towards Castiel. Castiel wasn’t sure whether to tug Dean away from the professor or throw himself at Dean here and now. 

“Oh, so you two aren’t...?” Balthazar asked, trailing off. His gaze shifted between the two men in front of him. Castiel prickled and opened his mouth to say something. 

Dean beat him to it, “No, we aren’t reenacting Julia Robert’s best movie, if that’s what you’re asking. Castiel is a fuckin’ great artist, and I’m going to see to it that he’s given the proper respect. That’s obviously not going to come from you and your fuck-all Institute, is it?” 

“Dean!” Castiel exclaimed, halfway between a laugh and a rebuff. A hand on his arm caught his attention. He looked up and saw the dark-haired woman from before smiling and beckoning him away from the conversation. 

He glanced back to where Dean was progressively getting angrier, and Balthazar was steadily getting more red in the face. He ducked out of their tense bubble and followed the woman to where the crowd was pouring out into the grounds. 

They wove between partygoers out on the concrete patio, some recognizing Castiel and reaching out to offer congratulations. The woman pressed on, and he had to offer his most polite avoidances to get away so he didn’t lose her in the crowd. 

She walked until they were far out of sight of the house. In the back of his head, Castiel hoped he wouldn’t end up missing an important internal organ later. She turned back while weaving through decorative hedges. “I didn’t mean to interrupt, I know Balthazar Reynolds can open many doors for those who are interested.” 

Castiel tripped over a stray branch Bobby must have missed, but recovered. “No, it’s... fine. He and I have had our history. We don’t get on too well.” 

“I realized I never properly introduced myself before I started bombarding you with questions about your work and personal life.” She stopped beneath one of the massive pear trees Dean had inexplicably planted all along the path and even down here further into the brush. They were lit up with countless strings of fairy lights. Dean wouldn’t say what possessed him to do it, he just answered with a sheepish smile and a “they’re just pretty.” 

The woman handed him a card. Emblazoned on it with silver script was the name Bela Talbot with a phone number printed at the bottom. 

“The fashion designer?” The woman smiled and extended her hand. 

“I’m pleased to know you have at least heard of me, Mr. Novak.” 

“Thank you for coming to my show, Ms. Talbot. It’s an honor.” 

Bela waved her hand dismissively. “Always a pleasure to check up on Dean Winchester and company. He certainly does keep a low profile out here, doesn’t he?”

“He likes his privacy.” 

“Yet you seem so comfortable out here in his space.” Bela eyed him with a knowing look. “Either you’ve made yourself indispensable enough to keep him company, or this sort of life is already familiar.” 

Castiel glanced down. “Dean and I... do share a comfortable relationship.” 

Bela’s eyebrow arched. “Oh, I do miss those days. Quite the cuddler, if memory serves. Not my cup of tea.” 

“Did Dean invite you?” Castiel honestly wasn’t sure if he should be excited or jealous that Dean’s ex—surely one of many—was at his show. 

“Dean knows I’m here, but I had to ask for my invitation. You should be worried, he talks endlessly about you.” She added with a salacious wink. Castiel fought down a blush, he refused to be embarrassed at his own show. 

“Not to be unkind, but why did you ask for an invite?” 

“You mean, why am I here?” Bela laughed, gorgeous in everything she did. Castiel didn’t answer. “I came to offer two pieces of advice and a business proposal.” 

“You better start with the business proposal first, just in case I have to make a dramatic exit.” 

Bela grinned, her slick red lipstick shining in the low light. “I want you to work with me. Help me cook up some designs the world will never see coming, and in screaming color. Your work is perfect for what I have in mind.” 

“Like a designer? Um, I don’t really know... anything about—“

“Think of it more like a design consultant. I have the fabrics, but I need the inspiration. Promise me you’ll think about it. Talk it over with your trophy husband and give me a call next week.” 

Castiel tucked her card securely in his pocket. He didn’t have a degree, but working with Bela Talbot’s house could open a lot of doors on its own. Not to mention the notoriety that came from even being in her presence, let alone on her staff. He promised to think about it. 

“You really liked my work that much?” He couldn’t help but ask, still a bit dumbstruck. 

Bela looked at him curiously and tilted her head. “Castiel, you have a wonderful knack for not knowing you have the kind of talent some people would kill for.” Castiel colored this time. “Yes, I wasn’t lying when I complimented the demon eyes piece. In fact, I’d love it for my lobby.” 

He couldn’t help but stare. His work in the lobby of one of the biggest names in the fashion business? “Y-you can have it.” 

“Don’t give it up that easily, darling.” Bela cautioned, mischief flickering her expression between seriousness and mirth. “If you’re good at something, attach a price tag.” 

“I don’t have any credentials, Ms. Talbot. I don’t want you to get the wrong idea here. I was kicked out of the Institute.” 

“Yes, Balthazar,” Bela pursed her lips. “I’ll have his head someday too, if I can manage it. The fashion department at the Institute really started churning out some atrocities when he took over, didn’t he? Such a pity... a fine establishment.” 

“Won’t that look pretty bad if you hire someone without a degree?”

“It’s my fashion house, darling. My name on the building and letterhead.” She curtsied and turned to leave. Castiel reached out and grabbed her arm, pulling it back just as quickly in case he got burned or smote or whatever. 

“What’s the advice?” 

Bela grinned like she hoped he would ask. She opened her bag and rummaged around. “The first is to take care of the people who love you. Fuck the rest of the world to hell, but pay special attention to those who pay good attention to you.” 

“That’s awfully emotional advice for... someone like you.”

“My reputation proceeds me,” Bela nodded sagely, as if she already knew. “But it is still true. I spent too many years pushing people away who cared for me. People who I knew I cared about as well, but was too lost in the tragedy of the art to show it.” She pulled out a pair of sky-high heels and slipped them on her feet. Castiel just noticed she had been barefoot the entire time. With her shoes on, she now towered over Castiel in more ways than one. 

“What’s the other advice?”

Her gentle smirk grew into a vicious smile, one that tore down corporations and left other fashion houses in ruin. “To never let anyone get in the way of what makes you happy.” With a final flourish, she turned and left to where a long black limousine must have been waiting for her the entire time just in front of the gates. Castiel watched her speed away, feeling mostly awestruck. 

He jumped when Dean pushed himself out of the brush to greet him. He dusted the twigs and leaves off his expensive suit as he looked where Castiel was gazing. 

“Cas! Thought I’d never find you out here!” He glanced around, “Am I already drunk or did I see you talking to Bela Talbot?” 

Castiel nodded vaguely. “Yes, she was kind enough to come to my show. She enjoyed my work a lot.” 

“Wondered why she was after me for an invite so bad. She wasn’t mean to you, was she?” Dean glanced sidelong at him, like he was wondering if he’d have to haul out the lawyers. 

“No, she offered me a job. In her design house.” 

“Huh. Is that... something you want?” 

Castiel pulled Dean out of the brush back to the path and towards the house. The lights were still high, and people swelled around the house and grounds like an unruly tide. He kept his arm firmly in Dean’s and relished the easy warmth between them. 

“I think it could make me happy. It certainly would pay well.” 

“Better than giving out blowjobs for fifty bucks on the street corner, huh?” The easy ribbing was a mark at how far they had come. Castiel wasn’t as ashamed of his past anymore. He knew who he was, and what he was good at. He was good at loving others, being loved in return, and creating art out of love. He felt good. 

“Dean, you don’t want to know what I had to do for a fifty.” 

Dean tucked his smile into Castiel’s hair and whispered low in his ear. “Actually, I totally do, and I want you to show me right here on the lawn.” 

Castiel grinned and pushed Dean sideways, pouncing when he stumbled—laughing the whole way—into the brush again. 

The End

**Notes for the Chapter:**

> Note: I have no ill will against the Art Institute of Chicago. I think it’s an amazing place, and I would willingly spend a week wandering around it if I could. There’s an amazing feeling of seeing so much history and passion encompassed in the walls of one building. Chicago itself holds so much wonder, and I was so glad to be able to take part in it. This story is a love letter to some of my favorite places on earth. Also, the Institute is running an exhibit on the Golden Era of Chicago fashion right now, and I like to think Bela got her way and kicked Balthazar out to get it underway. 
> 
> And so, this is the end. I’ve taken my sweet time about it—it’s been over a year—and at times I didn’t think I would make it to this point. This is, all at once, my finest work, the bane of my existence, my magnum opus. Thank you for reading. I’ll see you soon.
> 
> -azo


	22. Frequently Asked Questions

**Notes for the Chapter:**

> Hello everyone! What follows is some questions that were asked a few times over the course of the story between this page and my Tumblr. They're in no real order, but they do tie up some loose ends. 
> 
> Enjoy!
> 
> -azo

_Does Castiel ever graduate from the Institute?_  
\- He hasn’t yet, because he found himself a bit busier than he originally planned in between working with Bela and having rampant man sex with Dean at every opportunity. He doesn’t know if he ever will, but if he does, Dean is more than willing to be his one-man cheering section at the ceremony. Not that Sam, Sarah, Anna, Bobby, Missouri, Jo, Trevor, or Sr. Guerrero would ever let that happen. 

_What happened to the roadster?_  
\- It made its way back to the garage. It sits right next to the impala. Dean loves walking downstairs in the morning and just seeing the two of them, cozy next to each other. 

_Did Castiel go back to Chicago right away when Dean came to get him?_  
\- Nah, he had to show Dean the sights first! They walked around town, drank hot chocolate, visited the dance studio but didn’t stay long, and spent a LOT of time camped out in Castiel’s room. They had enough presence of mind to save their first official time for their bed back home though. 

_Does Castiel know that Balthazar was the man he was texting off the arrangement app?_  
\- No. Castiel never bothered to connect the two names, because it’s none of his business if his clients want to use their real names. Really, Castiel is lucky he never got the chance to meet his original date in the bar, because Balthazar probably would have kicked him out of the institute way sooner. They’re both in the dark about each other, but Balthazar has some issues of his own to work out. He’s married. 

_What color was the final piece that Castiel made for Dean?_  
\- It ended up being a comical and totally cliche piece with one green eye and one blue. At the art show, everyone was really confused about the meaning behind it, but Castiel and Dean loved seeing it and moved it right back down to the garage afterwards. 

_Did Sarah and Sam ever get pregnant?_  
\- Hell yeah they did! Sam found out the night of Castiel’s show. Sarah wasn’t taking any of the champagne, and when Sam asked, all she could do was smile hugely until Sam picked his jaw off the floor. They’re expecting a little girl in December. 

_How long did Bela and Dean date?_  
\- Not too long. They had an interesting relationship based more on camaraderie than any real affection. They both were eager to get the press off their backs and met at a holiday function for one of the bigger businesses in town. There was a lot of drunken sex and some accidental cuddling in between complaining about life in the spotlight. Bela liked that Dean lived out of the city and gave her space to think. Dean liked that Bela wasn’t after his money and was polite to Missouri and Bobby. They broke it off extremely amicably after they realized they had gone three months without any real romantic progress. 

_What does Anna do now?_   
\- she and Jo are having the time of their lives in small-town Kansas. They’re well on their way to graduation and have tentative plans to buy out the studio with Trevor. 

_What about Trevor?_  
\- He was a little bummed when Castiel moved away, but was very glad that Anna decided to come back. The owners of the studio are nearing retirement age and are looking for some young folks to keep up the good tradition. Anna sent him some of the keepsake postcards of the artwork from Castiel’s show and they’re tacked up in the cupboard that holds the tape player. 

_Whatever happened to that guy Castiel almost had sex with in the bar who was cheating on his wife?_  
\- They went to couples’ therapy and worked out that they were both unhappy in their current marriage. They parted as friends and he’s working on embracing his bisexuality. 

_Does Castiel ever reconnect with Sr. Guerrero?_  
\- Castiel loves visiting the bookstore and Anita. He stops by one day and Sr. Guerrero tells him how much better he looks and the whole story spills out. Sr. Guerrero makes him promise to bring Dean by one day. Castiel isn’t sure Dean’s ready for that. 

_Did Missouri ever get the leaky faucet fixed?_  
\- Bobby finally gave up and replaced the whole unit. He’s hiding that fact and is basking in Missouri’s awe of his apparent skill.


End file.
